1-Aryl-1,3,5-triazine-4-thione-2,6-diones, production thereof and use thereof as herbicides

ABSTRACT

Novel 1-aryl-4-thiotriazines I                    
     where the variables have the following meanings: 
     R 1 =H, NH 2 , C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl; 
     R 2 =H, NH 2 , C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl; 
     R 3 =H, halogen; 
     R 4 =CN, halogen; 
     Y=nitrogen, the methine group or, together with R 5 , a bridge &gt;C—O—C(R 6 )═N—; 
     R 5 =one of the meanings given in the description; 
     R 6 =H, halogen, substituted or unsubstituted C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 1 -C 6 -alkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 -cycloalkyl or C 3 -C 6 -cycloalkoxy; 
     their salts and enol ethers, the preparation of the novel compounds I and their use as herbicides.

The present invention relates to novel 1-aryl-4-thiotriazines of the formula I

in which the variables have the following meanings:

R¹ is hydrogen, amino, C₁-C₄-alkyl or C₁-C₄-haloalkyl;

R² is hydrogen, amino, C₁-C₄-alkyl or C₁-C₄-haloalkyl;

R³ is hydrogen or halogen;

R⁴ is cyano or halogen;

Y is nitrogen, the methine group or, together with R⁵, is a bridge >C—O—C(R⁶)═N—;

R⁵ is

1) hydrogen, hydroxyl, mercapto, nitro, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,

2) C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₃-C₆-cycloalkoxy, C₃-C₆-cycloalkylthio, C₂-C₆-alkenyloxy, C₂-C₆-alkenylthio, C₂-C₆-alkynyloxy or C₂-C₆-alkynylthio, it being possible, if desired, for each of these 8 radicals to have attached to it one of the following substituents: halogen, cyano, —CO—R⁸, —CO—OR⁸ or —CO—N(R⁸)—R⁹;

3) —COR¹¹, —C(R¹¹)(OR¹³)(OR¹⁴), —C(R¹¹)═C(R¹⁵)—CO—R¹⁶, —CH(R¹¹)—CH(R¹⁵)—CO—R¹⁶, —CO—OR²⁰, —C(R¹⁰)═N—OR⁷, —N(R²¹)—R²² or —CO—N(R²¹)—R²²;

R⁶ is hydrogen, halogen, C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, C₃-C₆-cycloalkyl or C₃-C₆-cycloalkoxy, it being possible for each of the last-mentioned 8 radicals, if desired, to have attached to it one to three substituents, in each case selected from the group consisting of halogen, C₁-C₆-alkoxy and —CO—OR^(8′);

R⁷ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, (C₁-C₆-alkoxy)carbonyl-C₁-C₆-alkyl, or benzyl;

R⁸, R^(8′) independently of one another are hydrogen, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, (C₁-C₆-alkoxy)carbonyl-C₁-C₆-alkyl, (C₃-C₆-alkenyloxy)carbonyl-C₁-C₆-alkyl, phenyl or phenyl-C₁-C₆-alkyl, it being possible for the phenyl group and the phenyl ring of the phenyl alkyl group to be unsubstituted or to have attached to them one to three radicals, in each case selected from the group consisting of halogen, nitro, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and (C₁-C₆-alkyl)carbonyl;

R⁹ is hydrogen or C₁-C₆-alkyl;

R¹⁰ is hydrogen, C₁-C₆-alkyl or C₁-C₆-alkoxy, it being possible for the 2 last-mentioned radicals to have attached to them one of the following substituents: C₁-C₆-alkoxy, (C₁-C₆-alkoxy)carbonyl or phenoxycarbonyl;

R¹¹ is hydrogen, C₁-C₆-alkyl or C₁-C₆-haloalkyl;

R¹³, R¹⁴ independently of one another are C₁-C₆-alkyl or together are a saturated 2- to 4-membered carbon chain which can have attached to it a C₁-C₆-alkyl radical;

R¹⁵ is hydrogen, cyano, halogen or C₁-C₆-alkyl;

R¹⁶ is O—R²³ or —N(R²¹)R²²;

R²⁰, R²³ independently of one another are hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl or C₂-C₆-alkynyl, it being possible for each of the last-mentioned 4 groups to have attached to it one or two of the following radicals: cyano, halogen, hydroxyl, hydroxycarbonyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, (C₁-C₆-alkyl)carbonyl, (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkyl)carbonyloxy, (C₃-C₆-alkenyloxy)carbonyl, (C₃-C₆-alkynyloxy)carbonyl or C₁-C₆-alkoxy-(C₁-C₆-alkoxy)carbonyl; or C₃-C₆-cycloalkyl, phenyl or phenyl-C₁-C₆-alkyl, where the phenyl rings can be unsubstituted or, in turn, can have attached to them one to three substituents, in each case selected from the group consisting of cyano, nitro, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and (C₁-C₆-alkoxy)carbonyl;

R²¹, R²² independently of one another are hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, (C₁-C₆-alkyl)carbonyl, (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkoxy)carbonyl-C₁-C₆-alkyl or C₁-C₆-alkylsulfonyl,

or R²¹ and R²² together with the joint nitrogen atom, are a saturated or unsaturated 4- to 7-membered aza heterocycle which, if desired, may contain one of the following members, in addition to carbon ring members: —O—, —S—, —N═, —NH— or —N(C₁-C₆-alkyl)—;

and the agriculturally useful salts and enol ethers of the compounds I.

Moreover, the invention relates to

the use of the compounds I as herbicides,

herbicidal compositions which comprise the compounds I as active substances,

processes for the preparation of the compounds I and of herbicidal compositions using the compounds I, and

methods of controlling undesirable vegetation using the compounds I.

DE-A 40 00 624 describes the specifically substituted 1-phenyltriazines as having a fungicidal action. A herbicidal action is not mentioned. Thiotriazines are not mentioned.

EP-A 640 600 describes substituted 4-thiotriazines which have a herbicidal action and which are 4-5-fused in the phenyl substituent.

The subject-matter of EP-A 584 655 and—to a small extent—also WO99/05125 is aryltriazinetriones of the type of the compounds I and their use as herbicides. A multiplicity of aryltriazines and arylthiotriazines fall under the general formulae; however, individual compounds having a thioketone group in the triazine moiety are not mentioned in either publication.

We have found that arylthiotriazines of the formula I as defined above have a particularly good herbicidal action. There have also been found herbicidal compositions which comprise the compounds I and which have a very good herbicidal action. Moreover, there have been found processes for the preparation of these compositions and methods for controlling undesirable vegetation using the compounds I.

Depending on the substitution pattern, the compounds of the formula I can contain one or more chiral centers, in which case they are present as enantiomer or diastereomer mixtures. In the case of compounds I which contain at least one olefinic residue, E/Z isomers may also be possible. Subject-matter of the invention are not only the pure enantiomers or diastereomers but also their mixtures.

Suitable amongst agriculturally useful salts are especially the salts of those cations, or the acid addition salts of those acids, whose cations or anions, respectively, do not adversely affect the herbicidal action of the compounds I. Thus, especially suitable cations are the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also the ammonium ion which, if desired, can have attached to it one to four C₁-C₄-alkyl substituents and/or one phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, moreover phosphonium ions, sulfonium ions, preferably tri(C₁-C₄-alkyl)sulfonium and sulfoxonium ions, preferably tri(C₁-C₄-alkyl)sulfoxonium.

Anions of useful acid addition salts are mainly chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C₁-C₄-alkanoic acids, preferably formate, acetate, propionate and butyrate.

The organic moieties mentioned in the definition of R¹ to R³, R⁵ to R²³ and on phenyl, cycloalkyl and heterocyclyl rings are collective terms for individual enumerations of the individual group members. All carbon chains, that is to say all (unsubstituted or substituted) alkyl, alkenyl or alkynyl moieties, can be straight-chain or branched.

Halogenated substituents preferably have attached to them one to five identical or different halogen atoms.

The meaning halogen is in each case fluorine, bromine, chlorine or iodine, in particular fluorine or chlorine.

Examples of other meanings are:

C₁-C₄-alkyl: CH₃, C₂H₅, n-propyl, CH(CH₃)₂, n-butyl, CH(CH₃)-C₂H₅, 2-methylpropyl or C(CH₃)₃, in particular CH₃, C₂H₅ or CH(CH₃)₂;

C₁-C₄-haloalkyl: a C₁-C₄-alkyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, e.g. CH₂F, CHF₂, CF₃, CH₂Cl, dichloromethyl, trichloromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, C₂F₅, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, CH₂-C₂F₅, CF₂-C₂F₅, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl, in particular CH₂F, CHF₂, CF₃, CH₂Cl, 2-fluoroethyl, 2-chloroethyl or 2,2,2-trifluoroethyl;

C₁-C₆-alkyl: C₁-C₄-alkyl as mentioned above and, for example, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl or 1-ethyl-2-methylpropyl, in particular CH₃, C₂H₅, n-propyl, CH(CH₃)₂, n-butyl, C(CH₃)₃, n-pentyl or n-hexyl;

C₁-C₆-haloalkyl: C₁-C₆-alkyl as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, e.g. one of the radicals mentioned under C₁-C₄-haloalkyl or 5-fluoro-1-pentyl, 5-chloro-1-pentyl, 5-bromo-1-pentyl, 5-iodo-1-pentyl, 5,5,5-trichloro-1-pentyl, undecafluoropentyl, 6-fluoro-1-hexyl, 6-chloro-1-hexyl, 6-bromo-1-hexyl, 6-iodo-1-hexyl, 6,6,6-trichloro-1-hexyl or dodecafluorohexyl, in particular chloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2-chloroethyl or 2,2,2-trifluoroethyl;

phenyl-C₁-C₆-alkyl: for example benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylprop-1-yl, 2-phenylprop-1-yl, 3-phenylprop-1-yl, 1-phenylbut-1-yl, 2-phenylbut-1-yl, 3-phenylbut-1-yl, 4-phenylbut-1-yl, 1-phenylbut-2-yl, 2-phenylbut-2-yl, 3-phenylbut-2-yl, 4-phenylbut-2-yl, 1-(phenylmethyl)eth-1-yl, 1-(phenylmethyl)-1-(methyl)eth-1-yl or 1-(phenylmethyl)prop-1-yl, in particular benzyl or 2-phenylethyl;

(C₁-C₆-alkyl)carbonyl: CO—CH₃, CO—C₂H₅, n-propylcarbonyl, 1-methylethylcarbonyl, n-butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl, 1,1-dimethylethylcarbonyl, n-pentylcarbonyl, 1-methylbutylcarbonyl, 2-methylbutylcarbonyl, 3-methylbutylcarbonyl, 1,1-dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl, 2,2-dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, n-hexylcarbonyl, 1-methylpentylcarbonyl, 2-methylpentylcarbonyl, 3-methylpentylcarbonyl, 4-methylpentylcarbonyl, 1,1-dimethylbutylcarbonyl, 1,2-dimethylbutylcarbonyl, 1,3-dimethylbutylcarbonyl, 2,2-dimethylbutylcarbonyl, 2,3-dimethylbutylcarbonyl, 3,3-dimethylbutylcarbonyl, 1-ethylbutylcarbonyl, 2-ethylbutylcarbonyl, 1,1,2-trimethylpropylcarbonyl, 1,2,2-trimethylpropylcarbonyl, 1-ethyl-1-methylpropylcarbonyl or 1-ethyl-2-methylpropylcarbonyl, in particular CO—CH₃, CO—C₂H₅ or CO—CH(CH₃)₂;

C₁-C₆-alkoxy: for example OCH₃, OC₂H₅, OCH₂—C₂H₅, OCH(CH₃)₂, n-butoxy, OCH(CH₃)—C₂H₅, OCH₂—CH(CH₃)₂, OC(CH₃)₃, n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, n-hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy, in particular OCH₃, OC₂H₅ or OCH(CH₃)₂;

(C₁-C₆-alkoxy)carbonyl: for example CO—OCH₃, CO—OC₂H₅, CO—CH₂—C₂H₅, CO—OCH(CH₃)₂, n-butoxycarbonyl, CO—OCH(CH₃)—C₂H₅, CO—OCH₂—CH(CH₃)₂, CO—OC(CH₃)₃, n-pentoxycarbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2,2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, n-hexoxycarbonyl, 1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1,1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl, 1,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl, 2,3-dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl, 1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl, 1,1,2-trimethylpropoxycarbonyl, 1,2,2-trimethylpropoxycarbonyl, 1-ethyl-1-methylpropoxycarbonyl or 1-ethyl-2-methylpropoxycarbonyl, in particular CO—OCH₃, CO—OC₂H₅, CO—OCH(CH₃)₂ or CO—CH₂—CH(CH₃)₂;

(C₁-C₆-alkoxy)carbonyloxy: methoxycarbonyloxy, ethoxycarbonyloxy, n-propoxycarbonyloxy, 1-methylethoxycarbonyloxy, n-butoxycarbonyloxy, 1-methylpropoxycarbonyloxy, 2-methylpropoxycarbonyloxy, 1,1-dimethylethoxycarbonyloxy, n-pentoxycarbonyloxy, 1-methylbutoxycarbonyloxy, 2-methylbutoxycarbonyloxy, 3-methylbutoxycarbonyloxy, 2,2-dimethylpropoxycarbonyloxy, 1-ethylpropoxycarbonyloxy, n-hexoxycarbonyloxy, 1,1-dimethylpropoxycarbonyloxy, 1,2-dimethylpropoxycarbonyloxy, 1-methylpentoxycarbonyloxy, 2-methylpentoxycarbonyloxy, 3-methylpentoxycarbonyloxy, 4-methylpentoxycarbonyloxy, 1,1-dimethylbutoxycarbonyloxy, 1,2-dimethylbutoxycarbonyloxy, 1,3-dimethylbutoxycarbonyloxy, 2,2-dimethylbutoxycarbonyloxy, 2,3-dimethylbutoxycarbonyloxy, 3,3-dimethylbutoxycarbonyloxy, 1-ethylbutoxycarbonyloxy, 2-ethylbutoxycarbonyloxy, 1,1,2-trimethylpropoxycarbonyloxy, 1,2,2-trimethylpropoxycarbonyloxy, 1-ethyl-1-methylpropoxycarbonyloxy or 1-ethyl-2-methylpropoxycarbonyloxy, in particular methoxycarbonyloxy, ethoxycarbonyloxy or 1-methylethoxycarbonyloxy;

C₁-C₆-alkylthio: SCH₃, SC₂H₅, SCH₂—C₂H₅, SCH(CH₃)₂, n-butylthio, 1-methylpropylthio, 2-methylpropylthio, SC(CH₃)₃, n-pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, n-hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio, in particular SCH₃ or SC₂H₅;

C₁-C₆-alkylsulfonyl: SO₂—CH₃, SO₂—C₂H₅, n-propylsulfonyl, SO₂—CH(CH₃)₂, n-butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, SO₂—C(CH₃)₃, n-pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, n-hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 11-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl or 1-ethyl-2-methylpropylsulfonyl,in particular SO₂—CH₃;

C₁-C₆-alkoxy-C₁-C₆-alkyl: C₁-C₆-alkyl which is substituted by C₁-C₆-alkoxy as mentioned above, i.e., for example, CH₂—OCH₃, CH₂—OC₂H₅, n-propoxymethyl, CH₂—OCH(CH₃)₂, n-butoxymethyl, (1-methylpropoxy)methyl, (2-methylpropoxy)methyl, CH₂—OC(CH₃)₃, 2-(methoxy)ethyl, 2-(ethoxy)ethyl, 2-(n-propoxy)ethyl, 2-(1-methylethoxy)ethyl, 2-(n-butoxy)ethyl, 2-(1-methylpropoxy)ethyl, 2-(2-methylpropoxy)ethyl, 2-(1,1-dimethylethoxy)ethyl, 2-(methoxy)propyl, 2-(ethoxy)propyl, 2-(n-propoxy)propyl, 2-(1-methylethoxy)propyl, 2-(n-butoxy)propyl, 2-(1-methylpropoxy)propyl, 2-(2-methylpropoxy)propyl, 2-(1,1-dimethylethoxy)propyl, 3-(methoxy)propyl, 3-(ethoxy)propyl, 3-(n-propoxy)propyl, 3-(1-methylethoxy)propyl, 3-(n-butoxy)propyl, 3-(1-methylpropoxy)propyl, 3-(2-methylpropoxy)propyl, 3-(1,1-dimethylethoxy)propyl, 2-(methoxy)butyl, 2-(ethoxy)butyl, 2-(n-propoxy)butyl, 2-(1-methylethoxy)butyl, 2-(n-butoxy)butyl, 2-(1-methylpropoxy)butyl, 2-(2-methylpropoxy)butyl, 2-(1,1-dimethylethoxy)butyl, 3-(methoxy)butyl, 3-(ethoxy)butyl, 3-(n-propoxy)butyl, 3-(1-methylethoxy)butyl, 3-(n-butoxy)butyl, 3-(1-methylpropoxy)butyl, 3-(2-methylpropoxy)butyl, 3-(1,1-dimethylethoxy)butyl, 4-(methoxy)butyl, 4-(ethoxy)butyl, 4-(n-propoxy)butyl, 4-(1-methylethoxy)butyl, 4-(n-butoxy)butyl, 4-(1-methylpropoxy)butyl, 4-(2-methylpropoxy)butyl or 4-(1,1-dimethylethoxy)butyl, in particular CH₂—OCH₃ or 2-methoxyethyl;

C₁-C₆-alkoxy-(C₁-C₆-alkoxy)carbonyl: (C₁-C₆-alkoxy)carbonyl which is substituted by (C₁-C₆-alkoxy) as mentioned above, e.g. CO—OCH₂—OCH₃, CO—OCH₂—OC₂H₅, CO—OCH₂—OCH₂—C₂H₅, CO—OCH₂—OCH(CH₃)₂, n-butoxymethoxycarbonyl, (1-methylpropoxy)methoxycarbonyl, CO—OCH₂—OCH₂—CH(CH₃)₂, CO—OCH₂—OC(CH₃)₃, 2-(methoxy)ethoxycarbonyl, 2-(ethoxy)ethoxycarbonyl, 2-(n-propoxy)ethoxycarbonyl, 2-(1-methylethoxy)ethoxycarbonyl, 2-(n-butoxy)ethoxycarbonyl, 2-(1-methylpropoxy)ethoxycarbonyl, 2-(2-methylpropoxy)ethoxycarbonyl, 2-(1,1-dimethylethoxy)ethoxycarbonyl, 2-(methoxy)propoxycarbonyl, 2-(ethoxy)propoxycarbonyl, 2-(n-propoxy)propoxycarbonyl, 2-(1-methylethoxy)propoxycarbonyl, 2-(n-butoxy)propoxycarbonyl, 2-(1-methylpropoxy)propoxycarbonyl, 2-(2-methylpropoxy)propoxycarbonyl, 2-(1,1-dimethylethoxy)propoxycarbonyl, 3-(methoxy)propoxycarbonyl, 3-(ethoxy)propoxycarbonyl, 3-(n-propoxy)propoxycarbonyl, 3-(1-methylethoxy)propoxycarbonyl, 3-(n-butoxy)propoxycarbonyl, 3-(1-methylpropoxy)propoxycarbonyl, 3-(2-methylpropoxy)propoxycarbonyl, 3-(1,1-dimethylethoxy)propoxycarbonyl, 2-(methoxy)butoxycarbonyl, 2-(ethoxy)butoxycarbonyl, 2-(n-propoxy)butoxycarbonyl, 2-(1-methylethoxy)butoxycarbonyl, 2-(n-butoxy)butoxycarbonyl, 2-(1-methylpropoxy)butoxycarbonyl, 2-(2-methylpropoxy)butoxycarbonyl, 2-(1,1-dimethylethoxy)butoxycarbonyl, 3-(methoxy)butoxycarbonyl, 3-(ethoxy)butoxycarbonyl, 3-(n-propoxy)butoxycarbonyl, 3-(1-methylethoxy)butoxycarbonyl, 3-(n-butoxy)butoxycarbonyl, 3-(1-methylpropoxy)butoxycarbonyl, 3-(2-methylpropoxy)butoxycarbonyl, 3-(1,1-dimethylethoxy)butoxycarbonyl, 4-(methoxy)butoxycarbonyl, 4-(ethoxy)butoxycarbonyl, 4-(n-propoxy)butoxycarbonyl, 4-(1-methylethoxy)butoxycarbonyl, 4-(n-butoxy)butoxycarbonyl, 4-(1-methylpropoxy)butoxycarbonyl, 4-(2-methylpropoxy)butoxycarbonyl, 4-(1,1-dimethylethoxy)butoxycarbonyl, 5-(methoxy)pentoxycarbonyl, 5-(ethoxy)pentoxycarbonyl, 5-(n-propoxy)pentoxycarbonyl, 5-(1-methylethoxy)pentoxycarbonyl, 5-(n-butoxy)pentoxycarbonyl, 5-(1-methylpropoxy)pentoxycarbonyl, 5-(2-methylpropoxy)pentoxycarbonyl, 5-(1,1-dimethylethoxy)pentoxycarbonyl, 6-(methoxy)hexoxycarbonyl, 6-(ethoxy)hexoxycarbonyl, 6-(n-propoxy)hexoxycarbonyl, 6-(1-methylethoxy)hexoxycarbonyl, 6-(n-butoxy)hexoxycarbonyl, 6-(1-methylpropoxy)hexoxycarbonyl, 6-(2-methylpropoxy)hexoxycarbonyl or 6-(1,1-dimethylethoxy)hexoxycarbonyl, in particular CO—OCH₂—OCH₃ or CO—OCH₂—OC₂H₅;

(C₁-C₆-alkoxy)carbonyl-C₁-C₆-alkyl: C₁-C₆-alkyl which is substituted by (C₁-C₆-alkoxy)carbonyl as mentioned above, e.g. methoxycarbonylmethyl, ethoxycarbonylmethyl, 1-(methoxycarbonyl)ethyl, 2-(methoxycarbonyl)ethyl, 2-(ethoxycarbonyl)ethyl, 3-(methoxycarbonyl)propyl, 4-(methoxycarbonyl)butyl, 5-(methoxycarbonyl)pentyl or 6-(methoxycarbonyl)hexyl;

C₃-C₆-alkenyl: for example prop-2-en-1-yl, n-buten-4-yl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, 2-buten-1-yl, n-penten-3-yl, n-penten-4-yl, 1-methylbut-2-en-1-yl, 2-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl, 1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl, 3-methylbut-3-en-1-yl, 1,1-dimethylprop-2-en-1-yl, 1,2-dimethylprop-2-en-1-yl, 1-ethylprop-2-en-1-yl, n-hex-3-en-1-yl, n-hex-4-en-1-yl, n-hex-5-en-1-yl, 1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl, 3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl, 1-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl, 3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl, 1,1-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl, 1,2-dimethylbut-2-en-1-yl, 1,2-dimethylbut-3-en-1-yl, 1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl, 2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-2-en-1-yl, 2,3-dimethylbut-3-en-1-yl, 3,3-dimethylbut-2-en-1-yl, 1-ethylbut-2-en-1-yl, 1-ethylbut-3-en-1-yl, 2-ethylbut-2-en-1-yl, 2-ethylbut-3-en-1-yl, 1,1,2-trimethylprop-2-en-1-yl, 1-ethyl-l-methylprop-2-en-1-yl or 1-ethyl-2-methylprop-2-en-1-yl, in particular prop-2-en-1-yl or n-buten-4-yl;

C₂-C₆-alkenyl: ethenyl or one of the radicals mentioned under C₃-C₆-alkenyl, in particular ethenyl or prop-2-en-1-yl;

C₃-C₆-alkenyloxy: prop-1-en-1-yloxy, prop-2-en-1-yloxy, 1-methylethenyloxy, n-buten-1-yloxy, n-buten-2-yloxy, n-buten-3-yloxy, 1-methylprop-1-en-1-yloxy, 2-methylprop-1-en-1-yloxy, 1-methylprop-2-en-1-yloxy, 2-methylprop-2-en-1-yloxy, n-penten-1-yloxy, n-penten-2-yloxy, n-penten-3-yloxy, n-penten-4-yloxy, 1-methylbut-1-en-1-yloxy, 2-methylbut-1-en-1-yloxy, 3-methylbut-1-en-1-yloxy, 1-methylbut-2-en-1-yloxy, 2-methylbut-2-en-1-yloxy, 3-methylbut-2-en-1-yloxy, 1-methylbut-3-en-1-yloxy, 2-methylbut-3-en-1-yloxy, 3-methylbut-3-en-1-yloxy, 1,1-dimethylprop-2-en-1-yloxy, 1,2-dimethylprop-1-en-1-yloxy, 1,2-dimethylprop-2-en-1-yloxy, 1-ethylprop-1-en-2-yloxy, 1-ethylprop-2-en-1-yloxy, n-hex-1-en-1-yloxy, n-hex-2-en-1-yloxy, n-hex-3-en-1-yloxy, n-hex-4-en-1-yloxy, n-hex-5-en-1-yloxy, 1-methylpent-1-en-1-yloxy, 2-methylpent-1-en-1-yloxy, 3-methylpent-1-en-1-yloxy, 4-methylpent-1-en-1-yloxy, 1-methylpent-2-en-1-yloxy, 2-methylpent-2-en-1-yloxy, 3-methylpent-2-en-1-yloxy, 4-methylpent-2-en-1-yloxy, 1-methylpent-3-en-1-yloxy, 2-methylpent-3-en-1-yloxy, 3-methylpent-3-en-1-yloxy, 4-methylpent-3-en-1-yloxy, 1-methylpent-4-en-1-yloxy, 2-methylpent-4-en-1-yloxy, 3-methylpent-4-en-1-yloxy, 4-methylpent-4-en-1-yloxy, 1,1-dimethylbut-2-en-1-yloxy, 1,1-dimethylbut-3-en-1-yloxy, 1,2-dimethylbut-1-en-1-yloxy, 1,2-dimethylbut-2-en-1-yloxy, 1,2-dimethylbut-3-en-1-yloxy, 1,3-dimethylbut-1-en-1-yloxy, 1,3-dimethylbut-2-en-1-yloxy, 1,3-dimethylbut-3-en-1-yloxy, 2,2-dimethylbut-3-en-1-yloxy, 2,3-dimethylbut-1-en-1-yloxy, 2,3-dimethylbut-2-en-1-yloxy, 2,3-dimethylbut-3-en-1-yloxy, 3,3-dimethylbut-1-en-1-yloxy, 3,3-dimethylbut-2-en-1-yloxy, 1-ethylbut-1-en-1-yloxy, 1-ethylbut-2-en-1-yloxy, 1-ethylbut-3-en-1-yloxy, 2-ethylbut-1-en-1-yloxy, 2-ethylbut-2-en-1-yloxy, 2-ethylbut-3-en-1-yloxy, 1,1,2-trimethylprop-2-en-1-yloxy, 1-ethyl-1-methylprop-2-en-1-yloxy, 1-ethyl-2-methylprop-1-en-1-yloxy or 1-ethyl-2-methylprop-2-en-1-yloxy, in particular prop-2-en-1-yloxy;

C₂-C₆-alkenyloxy: ethenyloxy or one of the radicals mentioned under C₃-C₆-alkenyloxy, in particular ethenyloxy or prop-2-en-1-yloxy;

C₂-C₆-alkenylthio: ethenylthio, prop-1-en-1-ylthio, prop-2-en-1-ylthio, 1-methylethenylthio, n-buten-1-ylthio, n-buten-2-ylthio, n-buten-3-ylthio, 1-methylprop-1-en-1-ylthio, 2-methylprop-1-en-1-ylthio, 1-methylprop-2-en-1-ylthio, 2-methylprop-2-en-1-ylthio, n-penten-1-ylthio, n-penten-2-ylthio, n-penten-3-ylthio, n-penten-4-ylthio, 1-methylbut-1-en-1-ylthio, 2-methylbut-1-en-1-ylthio, 3-methylbut-1-en-1-ylthio, 1-methylbut-2-en-1-ylthio, 2-methylbut-2-en-1-ylthio, 3-methylbut-2-en-1-ylthio, 1-methylbut-3-en-1-ylthio, 2-methylbut-3-en-1-ylthio, 3-methylbut-3-en-1-ylthio, 1,1-dimethylprop-2-en-1-ylthio, 1,2-dimethylprop-1-en-1-ylthio, 1,2-dimethylprop-2-en-1-ylthio, 1-ethylprop-1-en-2-ylthio, 1-ethylprop-2-en-1-ylthio, n-hex-1-en-1-ylthio, n-hex-2-en-1-ylthio, n-hex-3-en-1-ylthio, n-hex-4-en-1-ylthio, n-hex-5-en-1-ylthio, 1-methylpent-1-en-1-ylthio, 2-methylpent-1-en-1-ylthio, 3-methylpent-1-en-1-ylthio, 4-methylpent-1-en-1-ylthio, 1-methylpent-2-en-1-ylthio, 2-methylpent-2-en-1-ylthio, 3-methylpent-2-en-1-ylthio, 4-methylpent-2-en-1-ylthio, 1-methylpent-3-en-1-ylthio, 2-methylpent-3-en-1-ylthio, 3-methylpent-3-en-1-ylthio, 4-methylpent-3-en-1-ylthio, 1-methylpent-4-en-1-ylthio, 2-methylpent-4-en-1-ylthio, 3-methylpent-4-en-1-ylthio, 4-methylpent-4-en-1-ylthio, 1,1-dimethylbut-2-en-1-ylthio, 1,1-dimethylbut-3-en-1-ylthio, 1,2-dimethylbut-1-en-1-ylthio, 1,2-dimethylbut-2-en-1-ylthio, 1,2-dimethylbut-3-en-1-ylthio, 1,3-dimethylbut-1-en-1-ylthio, 1,3-dimethylbut-2-en-1-ylthio, 1,3-dimethylbut-3-en-1-ylthio, 2,2-dimethylbut-3-en-1-ylthio, 2,3-dimethylbut-1-en-1-ylthio, 2,3-dimethylbut-2-en-1-ylthio, 2,3-dimethylbut-3-en-1-ylthio, 3,3-dimethylbut-1-en-1-ylthio, 3,3-dimethylbut-2-en-1-ylthio, 1-ethylbut-1-en-1-ylthio, 1-ethylbut-2-en-1-ylthio, 1-ethylbut-3-en-1-ylthio, 2-ethylbut-1-en-1-ylthio, 2-ethylbut-2-en-1-ylthio, 2-ethylbut-3-en-1-ylthio, 1,1,2-trimethylprop-2-en-1-ylthio, 1-ethyl-1-methylprop-2-en-1-ylthio, 1-ethyl-2-methylprop-1-en-1-ylthio or 1-ethyl-2-methylprop-2-en-1-ylthio, in particular ethenylthio or prop-2-en-1-ylthio;

C₃-C₆-alkynyl: prop-1-yn-1-yl, prop-2-yn-1-yl, n-but-1-yn-1-yl, n-but-1-yn-3-yl, n-but-1-yn-4-yl, n-but-2-yn-1-yl, n-pent-1-yn-1-yl, n-pent-1-yn-3-yl, n-pent-1-yn-4-yl, n-pent-1-yn-5-yl, n-pent-2-yn-1-yl, n-pent-2-yn-4-yl, n-pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl, 3-methylbut-1-yn-4-yl, n-hex-1-yn-1-yl, n-hex-1-yn-3-yl, n-hex-1-yn-4-yl, n-hex-1-yn-5-yl, n-hex-1-yn-6-yl, n-hex-2-yn-1-yl, n-hex-2-yn-4-yl, n-hex-2-yn-5-yl, n-hex-2-yn-6-yl, n-hex-3-yn-1-yl, n-hex-3-yn-2-yl, 3-methylpent-1-yn-1-yl, 3-methylpent-1-yn-3-yl, 3-methylpent-1-yn-4-yl, 3-methylpent-1-yn-5-yl, 4-methylpent-1-yn-1-yl, 4-methylpent-2-yn-4-yl or 4-methylpent-2-yn-5-yl, in particular prop-2-yn-1-yl;

C₂-C₆-alkynyl: ethynyl or one of the radicals mentioned under C₃-C₆-alkynyl, in particular ethynyl or prop-2-yn-1-yl;

C₃-C₆-alkynyloxy: prop-1-yn-1-yloxy, prop-2-yn-1-yloxy, n-but-1-yn-1-yloxy, n-but-1-yn-3-yloxy, n-but-1-yn-4-yloxy, n-but-2-yn-1-yloxy, n-pent-1-yn-1-yloxy, n-pent-1-yn-3-yloxy, n-pent-1-yn-4-yloxy, n-pent-1-yn-5-yloxy, n-pent-2-yn-1-yloxy, n-pent-2-yn-4-yloxy, n-pent-2-yn-5-yloxy, 3-methylbut-1-yn-3-yloxy, 3-methylbut-1-yn-4-yloxy, n-hex-1-yn-1-yloxy, n-hex-1-yn-3-yloxy, n-hex-1-yn-4-yloxy, n-hex-1-yn-5-yloxy, n-hex-1-yn-6-yloxy, n-hex-2-yn-1-yloxy, n-hex-2-yn-4-yloxy, n-hex-2-yn-5-yloxy, n-hex-2-yn-6-yloxy, n-hex-3-yn-1-yloxy, n-hex-3-yn-2-yloxy, 3-methylpent-1-yn-1-yloxy, 3-methylpent-1-yn-3-yloxy, 3-methylpent-1-yn-4-yloxy, 3-methylpent-1-yn-5-yloxy, 4-methylpent-1-yn-1-yloxy, 4-methylpent-2-yn-4-yloxy or 4-methylpent-2-yn-5-yloxy, in particular prop-2-yn-1-yloxy;

C₂-C₆-alkynyloxy: ethynyloxy or one of the radicals mentioned under C₃-C₆-alkynyloxy, in particular ethynyloxy or prop-2-yn-1-yloxy;

C₂-C₆-alkynylthio: ethynylthio or one of the radicals mentioned under C₃-C₆-alkynylthio, in particular ethynylthio or prop-2-yn-1-ylthio;

(C₃₋C₆-alkenyloxy)carbonyl: prop-1-en-1-yloxycarbonyl, prop-2-en-1-yloxycarbonyl, 1-methylethenyloxycarbonyl, n-buten-1-yloxycarbonyl, n-buten-2-yloxycarbonyl, n-buten-3-yloxycarbonyl, 1-methylprop-1-en-1-yloxycarbonyl, 2-methylprop-1-en-1-yloxycarbonyl, 1-methylprop-2-en-1-yloxycarbonyl, 2-methylprop-2-en-1-yloxycarbonyl, n-penten-1-yloxycarbonyl, n-penten-2-yloxycarbonyl, n-penten-3-yloxycarbonyl, n-penten-4-yloxycarbonyl, 1-methylbut-1-en-1-yloxycarbonyl, 2-methylbut-1-en-1-yloxycarbonyl, 3-methylbut-1-en-1-yloxycarbonyl, 1-methylbut-2-en-1-yloxycarbonyl, 2-methylbut-2-en-1-yloxycarbonyl, 3-methylbut-2-en-1-yloxycarbonyl, 1-methylbut-3-en-1-yloxycarbonyl, 2-methylbut-3-en-1-yloxycarbonyl, 3-methylbut-3-en-1-yloxycarbonyl, 1,1-dimethylprop-2-en-1-yloxycarbonyl, 1,2-dimethylprop-1-en-1-yloxycarbonyl, 1,2-dimethylprop-2-en-1-yloxycarbonyl, 1-ethylprop-1-en-2-yloxycarbonyl, 1-ethylprop-2-en-1-yloxycarbonyl, n-hex-1-en-1-yloxycarbonyl, n-hex-2-en-1-yloxycarbonyl, n-hex-3-en-1-yloxycarbonyl, n-hex-4-en-1-yloxycarbonyl, n-hex-5-en-1-yloxycarbonyl, 1-methylpent-1-en-1-yloxycarbonyl, 2-methylpent-1-en-1-yloxycarbonyl, 3-methylpent-1-en-1-yloxycarbonyl, 4-methylpent-1-en-1-yloxycarbonyl, 1-methylpent-2-en-1-yloxycarbonyl, 2-methylpent-2-en-1-yloxycarbonyl, 3-methylpent-2-en-1-yloxycarbonyl, 4-methylpent-2-en-1-yloxycarbonyl, 1-methylpent-3-en-1-yloxycarbonyl, 2-methylpent-3-en-1-yloxycarbonyl, 3-methylpent-3-en-1-yloxycarbonyl, 4-methylpent-3-en-1-yloxycarbonyl, 1-methylpent-4-en-1-yloxycarbonyl, 2-methylpent-4-en-1-yloxycarbonyl, 3-methylpent-4-en-1-yloxycarbonyl, 4-methylpent-4-en-1-yloxycarbonyl, 1,1-dimethylbut-2-en-1-yloxycarbonyl, 1,1-dimethylbut-3-en-1-yloxycarbonyl, 1,2-dimethylbut-1-en-1-yloxycarbonyl, 1,2-dimethylbut-2-en-1-yloxycarbonyl, 1,2-dimethylbut-3-en-1-yloxycarbonyl, 1,3-dimethylbut-1-en-1-yloxycarbonyl, 1,3-dimethylbut-2-en-1-yloxycarbonyl, 1,3-dimethylbut-3-en-1-yloxycarbonyl, 2,2-dimethylbut-3-en-1-yloxycarbonyl, 2,3-dimethylbut-1-en-1-yloxycarbonyl, 2,3-dimethylbut-2-en-1-yloxycarbonyl, 2,3-dimethylbut-3-en-1-yloxycarbonyl, 3,3-dimethylbut-1-en-1-yloxycarbonyl, 3,3-dimethylbut-2-en-1-yloxycarbonyl, 1-ethylbut-1-en-1-yloxycarbonyl, 1-ethylbut-2-en-1-yloxycarbonyl, 1-ethylbut-3-en-1-yloxycarbonyl, 2-ethylbut-1-en-1-yloxycarbonyl, 2-ethylbut-2-en-1-yloxycarbonyl, 2-ethylbut-3-en-1-yloxycarbonyl, 1,1,2-trimethylprop-2-en-1-yloxycarbonyl, 1-ethyl-1-methylprop-2-en-1-yloxycarbonyl, 1-ethyl-2-methylprop-1-en-1-yloxycarbonyl or 1-ethyl-2-methylprop-2-en-1-yloxycarbonyl, in particular prop-2-en-1-yloxycarbonyl;

(C₃-C₆-alkenyloxy)carbonyl-C₁-C₆-alkyl: C₁-C₆-alkyl which is substituted by (C₃-C₆-alkenyloxy)carbonyl as mentioned above, preferably prop-2-en-1-yloxycarbonyl, e.g. prop-2-en-1-yl-oxycarbonylmethyl;

C₃-C₆-alkynyloxy)carbonyl: prop-1-yn-1-yloxycarbonyl, prop-2-yn-1-yloxycarbonyl, n-but-1-yn-1-yloxycarbonyl, n-but-1-yn-3-yloxycarbonyl, n-but-1-yn-4-yloxycarbonyl, n-but-2-yn-1-yloxycarbonyl, n-pent-1-yn-1-yloxycarbonyl, n-pent-1-yn-3-yloxycarbonyl, n-pent-1-yn-4-yloxycarbonyl, n-pent-1-yn-5-yloxycarbonyl, n-pent-2-yn-1-yloxycarbonyl, n-pent-2-yn-4-yloxycarbonyl, n-pent-2-yn-5-yloxycarbonyl, 3-methylbut-1-yn-3-yloxycarbonyl, 3-methylbut-1-yn-4-yloxycarbonyl, n-hex-1-yn-1-yloxycarbonyl, n-hex-1-yn-3-yloxycarbonyl, n-hex-1-yn-4-yloxycarbonyl, n-hex-1-yn-5-yloxycarbonyl, n-hex-1-yn-6-yloxycarbonyl, n-hex-2-yn-1-yloxycarbonyl, n-hex-2-yn-4-yloxycarbonyl, n-hex-2-yn-5-yloxycarbonyl, n-hex-2-yn-6-yloxycarbonyl, n-hex-3-yn-1-yloxycarbonyl, n-hex-3-yn-2-yloxycarbonyl, 3-methylpent-1-yn-1-yloxycarbonyl, 3-methylpent-1-yn-3-yloxycarbonyl, 3-methylpent-1-yn-4-yloxycarbonyl, 3-methylpent-1-yn-5-yloxycarbonyl, 4-methylpent-1-yn-1-yloxycarbonyl, 4-methylpent-2-yn-4-yloxycarbonyl or 4-methylpent-2-yn-5-yloxycarbonyl, in particular ethynyloxycarbonyl or prop-2-yn-1-yloxycarbonyl;

C₃-C₆-cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;

C₃-C₆-cycloalkyl-C₁-C₄-alkyl: for example cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1-(cyclopropyl)ethyl, 1-(cyclobutyl)ethyl, 1-(cyclopentyl)ethyl, 1-(cyclohexyl)ethyl, 2-(cyclopropyl)ethyl, 2-(cyclobutyl)ethyl, 2-(cyclopentyl)ethyl, 2-(cyclohexyl)-ethyl, 3-(cyclopropyl)propyl, 3-(cyclobutyl)propyl, 3-(cyclopentyl)propyl, 3-(cyclohexyl)propyl, 4-(cyclopropyl)butyl, 4-(cyclobutyl)butyl, 4-(cyclopentyl)butyl or 4-(cyclohexyl)butyl, in particular cyclopentylmethyl or cyclohexylmethyl;

C₃-C₆-cycloalkoxy: cyclopropyloxy, cyclobutyloxy, cyclopentyloxy or cyclohexyloxy;

C₃-C₆-cycloalkylthio: cyclopropylthio, cyclobutylthio, cyclopentylthio or cyclohexylthio.

4- to 7-membered aza heterocycles which, in addition to carbon ring members, may also comprise, as a ring member, an oxygen or sulfur atom, are, for example, azetidin-1-yl, pyrrolidin-1-yl, isoxazolidin-2-yl, isothiazolidin-2-yl, oxazolidin-3-yl, thiazolidin-3-yl, piperidin-1-yl, morpholin-1-yl, thiomorpholin-1-yl and azepin-1-yl.

With a view to the use of the 1-aryl-4-thiotriazines of the formula I according to the invention as herbicides, the variables preferably have the following meanings, in each case alone or in combination:

R¹ is hydrogen, amino or methyl, in particular methyl;

R² is hydrogen, amino or methyl, in particular methyl;

R³ is hydrogen or fluorine, in particular fluorine;

R⁴ is cyano or halogen, in particular

a) cyano;

b) chlorine;

Y is the methine group or, together with R⁵, is a bridge >C—O—C(R⁶)═N—, in particular

a) the methine group;

b) together with R⁵ a bridge >C—O—C(R⁶)═N—;

R⁵ is

1) on the one hand, hydrogen, nitro or halogen; on the other hand, C₁-C₆-alkyl or C₁-C₆-haloalkyl;

2) on the one hand, C₁-C₆-alkoxy or C₁-C₆-alkylthio, it being possible for each of these two radicals, if desired, to have attached to it one of the following substituents: cyano, —CO—R⁸, —CO—OR⁸ or —CO—N(R⁸)—R⁹, in particular methoxy, ethoxy, n-propyloxy, isopropoxy, methylthio, ethylthio, n-propylthio or isopropylthio, it being possible for each of these 8 radicals, if desired, to have attached to it a substituent —CO—OR^(8′) especially preferably (C₃-C₆-alkenyloxy)carbonylmethoxy, (C₃-C₆-alkynyloxy)carbonylmethoxy, 1-[(C₃-C₆-alkenyloxy)carbonyl]eth-1-yloxy, 1-[(C₃-C₆-alkynyloxy)carbonyl]eth-1-yloxy, C₁-C₄-alkoxy-(C₁-C₄-alkoxy)carbonylmethoxy, 1-[C₁-C₄-alkoxy-(C₁-C₄-alkoxy)carbonyl]eth-1-yloxy, (C₃-C₆-alkenyloxy)carbonylmethylthio, (C₃-C₆-alkynyloxy)carbonylmethylthio, 1-[(C₃-C₆-alkenyloxy)carbonyl]eth-1-ylthio, 1-[(C₃-C₆-alkynyloxy)carbonyl]eth-1-ylthio, C₁-C₄-alkoxy-(C₁-C₄-alkoxy)carbonylmethylthio or 1-[C₁-C₄-alkoxy-(C₁-C₄-alkoxy)carbonyl]eth-1-ylthio;

 on the other hand, C₃-C₆-cycloalkoxy, C₃-C₆-cycloalkylthio, C₂-C₆-alkenyloxy, C₂-C₆-alkenylthio, C₂-C₆-alkynyloxy or C₂-C₆-alkynylthio, it being possible for each of these 6 radicals, if desired, to have attached to it one of the following substituents: cyano, —CO—R⁸, —CO—OR⁸ or —CO—N(R⁸)—R⁹, in particular cyclopentyloxy, cyclopentylthio, allyloxy, allylthio, propargyloxy or propargylthio;

3) on the one hand, —CO—R¹¹, —C(R¹¹)═C(R¹⁵)—CO—R¹⁶, —CH(R¹¹)—CH(R¹⁵)—CO—R¹⁶, —C(R¹⁰)═N—OR⁷, —N(R²¹)—R²² or —CO—N(R²¹)—R²², in particular CHO, —CH═C(R¹⁵)—CO—R¹⁶, —CH₂-CH(R¹⁵)—CO-R¹⁶, —CH═N—OR⁷, —C(CH₃)═N—OR⁷, —N(R²¹)-R²² or —CO—N(R²¹)—R²²;

 on the other hand, —CO—OR²⁰;

R⁸ is hydrogen, C₃-C₆-cycloalkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl or C₁-C₄-alkoxy-C₁-C₄-alkyl, in particular C₃-C₆-alkenyl;

R^(8′) is hydrogen, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl or C₁-C₄-alkoxy-C₁-C₄-alkyl, in particular C₁-C₆-alkyl;

R⁹ is hydrogen;

R¹¹ is hydrogen;

R¹⁵ is hydrogen, halogen or C₁-C₆-alkyl, in particular hydrogen, chlorine, bromine or methyl, especially preferably chlorine;

R²⁰ is C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, (C₃-C₆-alkenyloxy)carbonylmethyl, (C₃-C₆-alkynyloxy)carbonylmethyl, 1-(C₃-C₆-alkenyloxy)carbonyl-eth-1-yl, 1-(C₃-C₆-alkynyloxy)carbonyl-eth-1-yl, C₁-C₄-alkoxy-(C₁-C₄-alkoxy)carbonylmethyl, 1-[C₁-C₄-alkoxy-(C₁-C₄-alkoxy)carbonyl]-eth-1-yl, 2-[(C₃-C₆-alkenyloxy)carbonyl]-prop-2-yl, C₃-C₆-cycloalkyl or C₃-C₆-cycloalkyl-C₁-C₄-alkyl;

R²³ is hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl or C₃-C₆-alkynyl, it being possible for the last-mentioned 3 groups to have attached to them in each case one of the following radicals:

C₁-C₆-alkoxy, (C₁-C₆-alkoxy)carbonyl or

(C₃-C₆-alkenyloxy)carbonyl.

Very specially preferred are the 1-aryl-4-thiotriazines of the formula Ia ({circumflex over (=)} I where R²=methyl and Y=the methine group)

in particular the compounds Ia.1 to Ia.720 which are listed in Table 1 below:

TABLE 1 No. R¹ R³ R⁴ R⁵ Ia.1 CH₃ F CN OCH(CH₃)—CO—OCH₃ Ia.2 CH₃ F CN OCH₂—C≡CH Ia.3 CH₃ F CN OCH(CH₃)—C≡CH Ia.4 CH₃ F CN OCH(CH₃)—CO—OCH₂—CH₂—OCH₃ Ia.5 CH₃ F CN CO—OCH₃ Ia.6 CH₃ F CN CO—OCH(CH₃)—CO—OCH₃ Ia.7 CH₃ F CN CO—OC(CH₃)₂—CO—OCH₃ Ia.8 CH₃ F CN CO—OCH(CH₃)—CO—OCH₂—CH═CH₂ Ia.9 CH₃ F CN CO—OC(CH₃)₂—CO—OCH₂—CH═CH₂ Ia.10 CH₃ F CN C(N—OCH₃)—OCH₂—CO—OCH₃ Ia.11 CH₃ F CN C(N—OCH₃)—OCH(CH₃)—CO—OCH₃ Ia.12 CH₃ F CN C(N—OCH₃)—OCH₂—CO—O(phenyl) Ia.13 CH₃ F CN CH═C(Cl)—CO—OCH₃ Ia.14 CH₃ F CN CH═C(CH₃)—CO—OCH₃ Ia.15 CH₃ F CN CH═C(Cl)—CO—OC₂H₅ Ia.16 CH₃ F CN CH═N—OCH₃ Ia.17 CH₃ F CN CH═N—OC₂H₅ Ia.18 CH₃ F CN CH═N—OCH₂—CH═CH₂ Ia.19 CH₃ F CN NH—SO₂—CH₃ Ia.20 CH₃ F CN NH—SO₂—C₂H₅ Ia.21 CH₃ F Cl OCH(CH₃)—CO—OCH₃ Ia.22 CH₃ F Cl OCH₂—C≡CH Ia.23 CH₃ F Cl OCH(CH₃)—C≡CH Ia.24 CH₃ F Cl OCH(CH₃)—CO—OCH₂—CH₂—OCH₃ Ia.25 CH₃ F Cl CO—OCH₃ Ia.26 CH₃ F Cl CO—OCH(CH₃)—CO—OCH₃ Ia.27 CH₃ F Cl CO—OC(CH₃)₂—CO—OCH₃ Ia.28 CH₃ F Cl CO—OCH(CH₃)—CO—OCH₂—CH═CH₂ Ia.29 CH₃ F Cl CO—OC(CH₃)₂—CO—OCH₂—CH═CH₂ Ia.30 CH₃ F Cl C(N—OCH₃)—OCH₂—CO—OCH₃ Ia.31 CH₃ F Cl C(N—OCH₃)—OCH(CH₃)—CO—OCH₃ Ia.32 CH₃ F Cl C(N—OCH₃)—OCH₂—CO—O(phenyl) Ia.33 CH₃ F Cl CH═C(Cl)—CO—OCH₃ Ia.34 CH₃ F Cl CH═C(CH₃)—CO—OCH₃ Ia.35 CH₃ F Cl CH═C(Cl)—CO—OC₂H₅ Ia.36 CH₃ F Cl CH═N—OCH₃ Ia.37 CH₃ F Cl CH═N—OC₂H₅ Ia.38 CH₃ F Cl CH═N—OCH₂—CH═CH₂ Ia.39 CH₃ F Cl NH—SO₂—CH₃ Ia.40 CH₃ F Cl NH—SO₂—C₂H₅ Ia.41 CH₃ H CN OCH(CH₃)—CO—OCH₃ Ia.42 CH₃ H CN OCH₂—C≡CH Ia.43 CH₃ H CN OCH(CH₃)—C≡CH Ia.44 CH₃ H CN OCH(CH₃)—CO—OCH₂—CH₂—OCH₃ Ia.45 CH₃ H CN CO—OCH₃ Ia.46 CH₃ H CN CO—OCH(CH₃)—CO—OCH₃ Ia.47 CH₃ H CN CO—OC(CH₃)₂—CO—OCH₃ Ia.48 CH₃ H CN CO—OCH(CH₃)—CO—OCH₂—CH═CH₂ Ia.49 CH₃ H CN CO—OC(CH₃)₂—CO—OCH₂—CH═CH₂ Ia.50 CH₃ H CN C(N—OCH₃)—OCH₂—CO—OCH₃ Ia.51 CH₃ H CN C(N—OCH₃)—OCH(CH₃)—CO—OCH₃ Ia.52 CH₃ H CN C(N—OCH₃)—OCH₂—CO—O(phenyl) Ia.53 CH₃ H CN CH═C(Cl)—CO—OCH₃ Ia.54 CH₃ H CN CH═C(CH₃)—CO—OCH₃ Ia.55 CH₃ H CN CH═C(Cl)—CO—OC₂H₅ Ia.56 CH₃ H CN CH═N—OCH₃ Ia.57 CH₃ H CN CH═N—OC₂H₅ Ia.58 CH₃ H CN CH═N—OCH₂—CH═CH₂ Ia.59 CH₃ H CN NH—SO₂—CH₃ Ia.60 CH₃ H CN NH—SO₂—C₂H₅ Ia.61 CH₃ H Cl OCH(CH₃)—CO—OCH₃ Ia.62 CH₃ H Cl OCH₂—C≡CH Ia.63 CH₃ H Cl OCH(CH₃)—C≡CH Ia.64 CH₃ H Cl OCH(CH₃)—CO—OCH₂—CH₂—OCH₃ Ia.65 CH₃ H Cl CO—OCH₃ Ia.66 CH₃ H Cl CO—OCH(CH₃)—CO—OCH₃ Ia.67 CH₃ H Cl CO—OC(CH₃)₂—CO—OCH₃ Ia.68 CH₃ H Cl CO—OCH(CH₃)—CO—OCH₂—CH═CH₂ Ia.69 CH₃ H Cl CO—OC(CH₃)₂—CO—OCH₂—CH═CH₂ Ia.70 CH₃ H Cl C(N—OCH₃)—OCH₂—CO—OCH₃ Ia.71 CH₃ H Cl C(N—OCH₃)—OCH(CH₃)—CO—OCH₃ Ia.72 CH₃ H Cl C(N—OCH₃)—OCH₂—CO—O(phenyl) Ia.73 CH₃ H Cl CH═C(Cl)—CO—OCH₃ Ia.74 CH₃ H Cl CH═C(CH₃)—CO—OCH₃ Ia.75 CH₃ H Cl CH═C(Cl)—CO—OC₂H₅ Ia.76 CH₃ H Cl CH═N—OCH₃ Ia.77 CH₃ H Cl CH═N—OC₂H₅ Ia.78 CH₃ H Cl CH═N—OCH₂—CH═CH₂ Ia.79 CH₃ H Cl NH—SO₂—CH₃ Ia.80 CH₃ H Cl NH—SO₂—C₂H₅ Ia.81 NH₂ F CN OCH(CH₃)—CO—OCH₃ Ia.82 NH₂ F CN OCH₂—C≡CH Ia.83 NH₂ F CN OCH(CH₃)—C≡CH Ia.84 NH₂ F CN OCH(CH₃)—CO—OCH₂—CH₂—OCH₃ Ia.85 NH₂ F CN CO—OCH₃ Ia.86 NH₂ F CN CO—OCH(CH₃)—CO—OCH₃ Ia.87 NH₂ F CN CO—OC(CH₃)₂—CO—OCH₃ Ia.88 NH₂ F CN CO—OCH(CH₃)—CO—OCH₂—CH═CH₂ Ia.89 NH₂ F CN CO—OC(CH₃)₂—CO—OCH₂—CH═CH₂ Ia.90 NH₂ F CN C(N—OCH₃)—OCH₂—CO—OCH₃ Ia.91 NH₂ F CN C(N—OCH₃)—OCH(CH₃)—CO—OCH₃ Ia.92 NH₂ F CN C(N—OCH₃)—OCH₂—CO—O(phenyl) Ia.93 NH₂ F CN CH═C(Cl)—CO—OCH₃ Ia.94 NH₂ F CN CH═C(CH₃)—CO—OCH₃ Ia.95 NH₂ F CN CH═C(Cl)—CO—OC₂H₅ Ia.96 NH₂ F CN CH═N—OCH₃ Ia.97 NH₂ F CN CH═N—OC₂H₅ Ia.98 NH₂ F CN CH═N—OCH₂—CH═CH₂ Ia.99 NH₂ F CN NH—SO₂—CH₃ Ia.100 NH₂ F CN NH—SO₂—C₂H₅ Ia.101 NH₂ F Cl OCH(CH₃)—CO—OCH₃ Ia.102 NH₂ F Cl OCH₂—C≡CH Ia.103 NH₂ F Cl OCH(CH₃)—C≡CH Ia.104 NH₂ F Cl OCH(CH₃)—CO—OCH₂—CH₂—OCH₃ Ia.105 NH₂ F Cl CO—OCH₃ Ia.106 NH₂ F Cl CO—OCH(CH₃)—CO—OCH₃ Ia.107 NH₂ F Cl CO—OC(CH₃)₂—CO—OCH₃ Ia.108 NH₂ F Cl CO—OCH(CH₃)—CO—OCH₂—CH═CH₂ Ia.109 NH₂ F Cl CO—OC(CH₃)₂—CO—OCH₂—CH═CH₂ Ia.110 NH₂ F Cl C(N—OCH₃)—OCH₂—CO—OCH₃ Ia.111 NH₂ F Cl C(N—OCH₃)—OCH(CH₃)—CO—OCH₃ Ia.112 NH₂ F Cl C(N—OCH₃)—OCH₂—CO—O(phenyl) Ia.113 NH₂ F Cl CH═C(Cl)—CO—OCH₃ Ia.114 NH₂ F Cl CH═C(CH₃)—CO—OCH₃ Ia.115 NH₂ F Cl CH═C(Cl)—CO—OC₂H₅ Ia.116 NH₂ F Cl CH═N—OCH₃ Ia.117 NH₂ F Cl CH═N—OC₂H₅ Ia.118 NH₂ F Cl CH═N—OCH₂—CH═CH₂ Ia.119 NH₂ F Cl NH—SO₂—CH₃ Ia.120 NH₂ F Cl NH—SO₂—C₂H₅ Ia.121 NH₂ H CN OCH(CH₃)—CO—OCH₃ Ia.122 NH₂ H CN OCH₂—C≡CH Ia.123 NH₂ H CN OCH(CH₃)—C≡CH Ia.124 NH₂ H CN OCH(CH₃)—CO—OCH₂—CH₂—OCH₃ Ia.125 NH₂ H CN CO—OCH₃ Ia.126 NH₂ H CN CO—OCH(CH₃)—CO—OCH₃ Ia.127 NH₂ H CN CO—OC(CH₃)₂—CO—OCH₃ Ia.128 NH₂ H CN CO—OCH(CH₃)—CO—OCH₂—CH═CH₂ Ia.129 NH₂ H CN CO—OC(CH₃)₂—CO—OCH₂—CH═CH₂ Ia.130 NH₂ H CN C(N—OCH₃)—OCH₂—CO—OCH₃ Ia.131 NH₂ H CN C(N—OCH₃)—OCH(CH₃)—CO—OCH₃ Ia.132 NH₂ H CN C(N—OCH₃)—OCH₂—CO—O(phenyl) Ia.133 NH₂ H CN CH═C(Cl)—CO—OCH₃ Ia.134 NH₂ H CN CH═C(CH₃)—CO—OCH₃ Ia.135 NH₂ H CN CH═C(Cl)—CO—OC₂H₅ Ia.136 NH₂ H CN CH═N—OCH₃ Ia.137 NH₂ H CN CH═N—OC₂H₅ Ia.138 NH₂ H CN CH═N—OCH₂—CH═CH₂ Ia.139 NH₂ H CN NH—SO₂—CH₃ Ia.140 NH₂ H CN NH—SO₂—C₂H₅ Ia.141 NH₂ H Cl OCH(CH₃)—CO—OCH₃ Ia.142 NH₂ H Cl OCH₂—C≡CH Ia.143 NH₂ H Cl OCH(CH₃)—C≡CH Ia.144 NH₂ H Cl OCH(CH₃)—CO—OCH₂—CH₂—OCH₃ Ia.145 NH₂ H Cl CO—OCH₃ Ia.146 NH₂ H Cl CO—OCH(CH₃)—CO—OCH₃ Ia.147 NH₂ H Cl CO—OC(CH₃)₂—CO—OCH₃ Ia.148 NH₂ H Cl CO—OCH(CH₃)—CO—OCH₂—CH═CH₂ Ia.149 NH₂ H Cl CO—OC(CH₃)₂—CO—OCH₂—CH═CH₂ Ia.150 NH₂ H Cl C(N—OCH₃)—OCH₂—CO—OCH₃ Ia.151 NH₂ H Cl C(N—OCH₃)—OCH(CH₃)—CO—OCH₃ Ia.152 NH₂ H Cl C(N—OCH₃)—OCH₂—CO—O(phenyl) Ia.153 NH₂ H Cl CH═C(Cl)—CO—OCH₃ Ia.154 NH₂ H Cl CH═C(CH₃)—CO—OCH₃ Ia.155 NH₂ H Cl CH═C(Cl)—CO—OC₂H₅ Ia.156 NH₂ H Cl CH═N—OCH₃ Ia.157 NH₂ H Cl CH═N—OC₂H₅ Ia.158 NH₂ H Cl CH═N—OCH₂—CH═CH₂ Ia.159 NH₂ H Cl NH—SO₂—CH₃ Ia.160 NH₂ H Cl NH—SO₂—C₂H₅ Ia.161 CH₃ F Cl OCH₃ Ia.162 CH₃ F Cl OCH(CH₃)₂ Ia.163 CH₃ F Cl OCH₂—CH═CH₂ Ia.164 CH₃ F Cl O-cyclopentyl Ia.165 CH₃ F Cl OCH₂—CO—OCH₃ Ia.166 CH₃ F Cl OCH₂—CO—OCH₂—CH═CH₂ Ia.167 CH₃ F Cl OCH₂—CO—OCH₂—CH═CH—CH₃ Ia.168 CH₃ F Cl OCH₂—CO—OCH₂—CH₂—CH═CH₂ Ia.169 CH₃ F Cl OCH₂—CO—OCH₂—CH═C(CH₃)₂ Ia.170 CH₃ F Cl OCH₂—CO—OCH₂—C≡CH Ia.171 CH₃ F Cl OCH₂—CO—OCH₂CH₂—C≡CH Ia.172 CH₃ F Cl OCH₂—CO—O-cyclopentyl Ia.173 CH₃ F Cl OCH₂—CO—OCH₂CH₂—OCH₃ Ia.174 CH₃ F Cl OCH₂—CO—OCH₂CH₂—OC₂H₅ Ia.175 CH₃ F Cl OCH₂—CO—OCH₂-cyclopropyl Ia.176 CH₃ F Cl OCH₂—CO—OCH₂-cyclobutyl Ia.177 CH₃ F Cl OCH₂—CO—OCH₂-cyclopentyl Ia.178 CH₃ F Cl OCH₂—CO—OCH₂-cyclohexyl Ia.179 CH₃ F Cl OCH₂—CO—NH—CH₃ Ia.180 CH₃ F Cl OCH₂—CO—N(CH₃)₂ Ia.181 CH₃ F Cl OCH(CH₃)—CO—OCH₂—CH═CH₂ Ia.182 CH₃ F Cl OCH(CH₃)—CO—OCH₂—CH═CH—CH₃ Ia.183 CH₃ F Cl OCH(CH₃)—CO—OCH₂CH₂—CH═CH₂ Ia.184 CH₃ F Cl OCH(CH₃)—CO—OCH₂—CH═C(CH₃)₂ Ia.185 CH₃ F Cl OCH(CH₃)—CO—OCH₂—C≡CH Ia.186 CH₃ F Cl OCH(CH₃)—CO—O—CH₂CH₂—C≡CH Ia.187 CH₃ F Cl OCH(CH₃)—CO—O-cyclopentyl Ia.188 CH₃ F Cl OCH(CH₃)—CO—OCH₂CH₂—OC₂H₅ Ia.189 CH₃ F Cl OCH(CH₃)—CO—OCH₂-cyclopropyl Ia.190 CH₃ F Cl OCH(CH₃)—CO—OCH₂-cyclobutyl Ia.191 CH₃ F Cl OCH(CH₃)—CO—OCH₂-cyclopentyl Ia.192 CH₃ F Cl OCH(CH₃)—CO—OCH₂-cyclohexyl Ia.193 CH₃ F Cl OCH(CH₃)—CO—NH—CH₃ Ia.194 CH₃ F Cl OCH(CH₃)—CO—N(CH₃)₂ Ia.195 CH₃ F Cl OC(CH₃)₂—CO—OCH₃ Ia.196 CH₃ F Cl OC(CH₃)₂—CO—OCH₂—CH═CH₂ Ia.197 CH₃ F Cl OC(CH₃)₂—CO—OCH₂—C≡CH Ia.198 CH₃ F Cl OC(CH₃)₂—CO—O-cyclopentyl Ia.199 CH₃ F Cl OC(CH₃)₂—CO—OCH₂CH₂—OCH₃ Ia.200 CH₃ F Cl COOH Ia.201 CH₃ F Cl CO—OCH(CH₃)₂ Ia.202 CH₃ F Cl CO—OCH₂—CH═CH₂ Ia.203 CH₃ F Cl CO—OCH₂—C≡CH Ia.204 CH₃ F Cl CO—O-cyclopentyl Ia.205 CH₃ F Cl CO—OCH₂—CO—OCH₃ Ia.206 CH₃ F Cl CO—OCH₂—CO—OCH₂—CH═CH₂ Ia.207 CH₃ F Cl CO—OCH₂CO—OCH₂—C≡CH Ia.208 CH₃ F Cl CO—OCH₂CO—OCH₂CH₂—OCH₃ Ia.209 CH₃ F Cl CO—OCH(CH₃)—CO—OCH₂—C≡CH Ia.210 CH₃ F Cl CO—OCH(CH₃)—CO—OCH₂CH₂—OCH₃ Ia.211 CH₃ F Cl CO—OC(CH₃)₂—CO—OCH₂—C≡CH Ia.212 CH₃ F Cl CO—OC(CH₃)₂—CO—OCH₂CH₂—OCH₃ Ia.213 CH₃ F Cl CO—NH—CH₂—CO—OCH₃ Ia.214 CH₃ F Cl CO—NH—CH₂—CO—OCH₂—CH═CH₂ Ia.215 CH₃ F Cl CO—NH—CH₂—CO—OCH₂CH₂—OCH₃ Ia.216 CH₃ F Cl CO—NH—CH(CH₃)—CO—OCH₃ Ia.217 CH₃ F Cl CO—NH—CH(CH₃)—CO—OCH₂—CH═CH₂ Ia.218 CH₃ F Cl CO—NH—CH(CH₃)—CO—OCH₂CH₂—OCH₃ Ia.219 CH₃ F Cl CO—N(CH₃)—CH₂—CO—OCH₃ Ia.220 CH₃ F Cl CO—N(CH₃)—CH₂—CO—OCH₂—CH═CH₂ Ia.221 CH₃ F Cl CO—N(CH₃)—CH₂—CO—OCH₂CH₂—OCH₃ Ia.222 CH₃ F Cl CO—N(CH₃)—CH(CH₃)COO—CH₃ Ia.223 CH₃ F Cl CO—N(CH₃)—CH(CH₃)COO—CH₂CH═CH₂ Ia.224 CH₃ F Cl CO—N(CH₃)—CH(CH₃)COO—CH₂CH₂OCH₃ Ia.225 CH₃ F Cl CH═C(Cl)—CO—OCH₂—CH═CH₂ Ia.226 CH₃ F Cl CH═C(Cl)—CO—OCH₂—C≡CH Ia.227 CH₃ F Cl CH═C(Cl)—CO—OCH₂—CO—OCH₃ Ia.228 CH₃ F Cl CH═C(Cl)—CO—OCH(CH₃)—CO—OCH₃ Ia.229 CH₃ F Cl CH═C(Cl)—CO—N(CH₃)—CH₂—CO—OCH₃ Ia.230 CH₃ F Cl CH═C(Cl)—CO—NH—CH(CH₃)—CO—OCH₃ Ia.231 CH₃ F CN OCH₃ Ia.232 CH₃ F CN OCH(CH₃)₂ Ia.233 CH₃ F CN O—CH₂CH═CH₂ Ia.234 CH₃ F CN O-cyclopentyl Ia.235 CH₃ F CN OCH₂—CO—OCH₃ Ia.236 CH₃ F CN OCH₂—CO—OCH₂—CH═CH₂ Ia.237 CH₃ F CN OCH₂—CO—OCH₂CH═CH—CH₃ Ia.238 CH₃ F CN OCH₂—CO—OCH₂CH₂—CH═CH₂ Ia.239 CH₃ F CN OCH₂—CO—OCH₂—CH═C(CH₃)₂ Ia.240 CH₃ F CN OCH₂—CO—OCH₂—C≡CH Ia.241 CH₃ F CN OCH₂—CO—OCH₂CH₂—C≡CH Ia.242 CH₃ F CN OCH₂—CO—O-cyclopentyl Ia.243 CH₃ F CN OCH₂—CO—OCH₂CH₂—OCH₃ Ia.244 CH₃ F CN OCH₂—CO—OCH₂CH₂—OC₂H₅ Ia.245 CH₃ F CN OCH₂—CO—OCH₂-cyclopropyl Ia.246 CH₃ F CN OCH₂—CO—OCH₂-cyclobutyl Ia.247 CH₃ F CN OCH₂—CO—OCH₂-cyclopentyl Ia.248 CH₃ F CN OCH₂—CO—OCH₂-cyclohexyl Ia.249 CH₃ F CN OCH₂—CO—NH—CH₃ Ia.250 CH₃ F CN OCH₂—CO—N(CH₃)₂ Ia.251 CH₃ F CN OCH(CH₃)—CO—OCH₂—CH═CH₂ Ia.252 CH₃ F CN OCH(CH₃)—CO—OCH₂—CH═CH—CH₃ Ia.253 CH₃ F CN OCH(CH₃)—CO—OCH₂CH₂—CH═CH₂ Ia.254 CH₃ F CN OCH(CH₃)—CO—OCH₂—CH═C(CH₃)₂ Ia.255 CH₃ F CN OCH(CH₃)—CO—OCH₂—C≡CH Ia.256 CH₃ F CN OCH(CH₃)—CO—OCH₂CH₂—C≡CH Ia.257 CH₃ F CN OCH(CH₃)—CO—O-cyclopentyl Ia.258 CH₃ F CN OCH(CH₃)—CO—OCH₂CH₂—OC₂H₅ Ia.259 CH₃ F CN OCH(CH₃)—CO—OCH₂-cyclopropyl Ia.260 CH₃ F CN OCH(CH₃)—CO—OCH₂-cyclobutyl Ia.261 CH₃ F CN OCH(CH₃)—CO—OCH₂-cyclopentyl Ia.262 CH₃ F CN OCH(CH₃)—CO—OCH₂-cyclohexyl Ia.263 CH₃ F CN OCH(CH₃)—CO—NH—CH₃ Ia.264 CH₃ F CN OCH(CH₃)—CO—N(CH₃)₂ Ia.265 CH₃ F CN OC(CH₃)₂—CO—OCH₃ Ia.266 CH₃ F CN OC(CH₃)₂—CO—OCH₂—CH═CH₂ Ia.267 CH₃ F CN OC(CH₃)₂—CO—OCH₂—C≡CH Ia.268 CH₃ F CN OC(CH₃)₂—CO—O-cyclopentyl Ia.269 CH₃ F CN OC(CH₃)₂—CO—OCH₂CH₂—OCH₃ Ia.270 CH₃ F CN COOH Ia.271 CH₃ F CN CO—OCH(CH₃)₂ Ia.272 CH₃ F CN CO—OCH₂—CH═CH₂ Ia.273 CH₃ F CN CO—OCH₂—C≡CH Ia.274 CH₃ F CN CO—O-cyclopentyl Ia.275 CH₃ F CN CO—OCH₂—CO—OCH₃ Ia.276 CH₃ F CN CO—OCH₂—CO—OCH₂—CH═CH₂ Ia.277 CH₃ F CN CO—OCH₂—CO—OCH₂—C≡CH Ia.278 CH₃ F CN CO—OCH₂—CO—OCH₂CH₂—OCH₃ Ia.279 CH₃ F CN CO—OCH(CH₃)—CO—OCH₂—C≡CH Ia.280 CH₃ F CN CO—OCH(CH₃)—CO—OCH₂CH₂—OCH₃ Ia.281 CH₃ F CN CO—OC(CH₃)₂—CO—OCH₂—C≡CH Ia.282 CH₃ F CN CO—OC(CH₃)₂—CO—OCH₂CH₂—OCH₃ Ia.283 CH₃ F CN CO—NH—CH₂—CO—OCH₃ Ia.284 CH₃ F CN CO—NH—CH₂—CO—OCH₂—CH═CH₂ Ia.285 CH₃ F CN CO—NH—CH₂—CO—OCH₂CH₂—OCH₃ Ia.286 CH₃ F CN CO—NH—CH(CH₃)—CO—OCH₃ Ia.287 CH₃ F CN CO—NH—CH(CH₃)—CO—OCH₂—CH═CH₂ Ia.288 CH₃ F CN CO—NH—CH(CH₃)—CO—OCH₂CH₂—OCH₃ Ia.289 CH₃ F CN CO—N(CH₃)—CH₂—CO—OCH₃ Ia.290 CH₃ F CN CO—N(CH₃)—CH₂—CO—OCH₂—CH═CH₂ Ia.291 CH₃ F CN CO—N(CH₃)—CH₂—CO—OCH₂CH₂—OCH₃ Ia.292 CH₃ F CN CO—N(CH₃)—CH(CH₃)—CO—OCH₃ Ia.293 CH₃ F CN CO—N(CH₃)—CH(CH₃)—CO—OCH₂—CH═CH₂ Ia.294 CH₃ F CN CO—N(CH₃)—CH(CH₃)—CO—OCH₂CH₂—OCH₃ Ia.295 CH₃ F CN CH═C(Cl)—CO—OCH₂—CH═CH₂ Ia.296 CH₃ F CN CH═C(Cl)—CO—OCH₂—C≡CH Ia.297 CH₃ F CN CH═C(Cl)—CO—OCH₂—CO—OCH₃ Ia.298 CH₃ F CN CH═C(Cl)—CO—OCH(CH₃)—CO—OCH₃ Ia.299 CH₃ F CN CH═C(Cl)—CO—N(CH₃)—CH₂—CO—OCH₃ Ia.300 CH₃ F CN CH═C(Cl)—CO—NH—CH(CH₃)—CO—OCH₃ Ia.301 CH₃ H Cl OCH₃ Ia.302 CH₃ H Cl OCH(CH₃)₂ Ia.303 CH₃ H Cl O—CH₂—CH═CH₂ Ia.304 CH₃ H Cl O-cyclopentyl Ia.305 CH₃ H Cl OCH₂—CO—OCH₃ Ia.306 CH₃ H Cl OCH₂—CO—OCH₂—CH═CH₂ Ia.307 CH₃ H Cl OCH₂—CO—OCH₂—CH═CH—CH₃ Ia.308 CH₃ H Cl OCH₂—CO—OCH₂CH₂—CH═CH₂ Ia.309 CH₃ H Cl OCH₂—CO—OCH₂—CH═C(CH₃)₂ Ia.310 CH₃ H Cl OCH₂—CO—OCH₂—C≡CH Ia.311 CH₃ H Cl OCH₂—CO—OCH₂CH₂—C≡CH Ia.312 CH₃ H Cl OCH₂—CO—O-cyclopentyl Ia.313 CH₃ H Cl OCH₂—CO—OCH₂CH₂—OCH₃ Ia.314 CH₃ H Cl OCH₂—CO—OCH₂CH₂—OC₂H₅ Ia.315 CH₃ H Cl OCH₂—CO—OCH₂-cyclopropyl Ia.316 CH₃ H Cl OCH₂—CO—OCH₂-cyclobutyl Ia.317 CH₃ H Cl OCH₂—CO—OCH₂-cyclopentyl Ia.318 CH₃ H Cl OCH₂—CO—OCH₂-cyclohexyl Ia.319 CH₃ H Cl OCH₂—CO—NH—CH₃ Ia.320 CH₃ H Cl OCH₂—CO—N(CH₃)₂ Ia.321 CH₃ H Cl OCH(CH₃)—CO—OCH₂—CH═CH₂ Ia.322 CH₃ H Cl OCH(CH₃)—CO—OCH₂—CH═CH—CH₃ Ia.323 CH₃ H Cl OCH(CH₃)—CO—OCH₂CH₂—CH═CH₂ Ia.324 CH₃ H Cl OCH(CH₃)—CO—OCH₂—CH═C(CH₃)₂ Ia.325 CH₃ H Cl OCH(CH₃)—CO—OCH₂—C≡CH Ia.326 CH₃ H Cl OCH(CH₃)—CO—OCH₂CH₂—C≡CH Ia.327 CH₃ H Cl OCH(CH₃)—CO—O-cyclopentyl Ia.328 CH₃ H Cl OCH(CH₃)—CO—OCH₂CH₂—OC₂H₅ Ia.329 CH₃ H Cl OCH(CH₃)—CO—OCH₂-cyclopropyl Ia.330 CH₃ H Cl OCH(CH₃)—CO—OCH₂-cyclobutyl Ia.331 CH₃ H Cl OCH(CH₃)—CO—OCH₂-cyclopentyl Ia.332 CH₃ H Cl OCH(CH₃)—CO—OCH₂-cyclohexyl Ia.333 CH₃ H Cl OCH(CH₃)—CO—NH—CH₃ Ia.334 CH₃ H Cl OCH(CH₃)—CO—N(CH₃)₂ Ia.335 CH₃ H Cl OC(CH₃)₂—CO—OCH₃ Ia.336 CH₃ H Cl OC(CH₃)₂—CO—OCH₂—CH═CH₂ Ia.337 CH₃ H Cl OC(CH₃)₂—CO—OCH₂—C≡CH Ia.338 CH₃ H Cl OC(CH₃)₂—CO—O-cyclopentyl Ia.339 CH₃ H Cl OC(CH₃)₂—CO—OCH₂CH₂—OCH₃ Ia.340 CH₃ H Cl COOH Ia.341 CH₃ H Cl CO—OCH(CH₃)₂ Ia.342 CH₃ H Cl CO—OCH₂—CH═CH₂ Ia.343 CH₃ H Cl CO—OCH₂—C≡CH Ia.344 CH₃ H Cl CO—O-cyclopentyl Ia.345 CH₃ H Cl CO—OCH₂—CO—OCH₃ Ia.346 CH₃ H Cl CO—OCH₂—CO—OCH₂—CH═CH₂ Ia.347 CH₃ H Cl CO—OCH₂—CO—OCH₂—C≡CH Ia.348 CH₃ H Cl CO—OCH₂—CO—OCH₂CH₂—OCH₃ Ia.349 CH₃ H Cl CO—OCH(CH₃)—CO—OCH₂—C≡CH Ia.350 CH₃ H Cl CO—OCH(CH₃)—CO—OCH₂CH₂—OCH₃ Ia.351 CH₃ H Cl CO—OC(CH₃)₂—CO—OCH₂—C≡CH Ia.352 CH₃ H Cl CO—OC(CH₃)₂—CO—OCH₂CH₂—OCH₃ Ia.353 CH₃ H Cl CO—NH—CH₂—CO—OCH₃ Ia.354 CH₃ H Cl CO—NH—CH₂—CO—OCH₂—CH═CH₂ Ia.355 CH₃ H Cl CO—NH—CH₂—CO—OCH₂CH₂—OCH₃ Ia.356 CH₃ H Cl CO—NH—CH(CH₃)—CO—OCH₃ Ia.357 CH₃ H Cl CO—NH—CH(CH₃)—CO—OCH₂—CH═CH₂ Ia.358 CH₃ H Cl CO—NH—CH(CH₃)—CO—OCH₂CH₂—OCH₃ Ia.359 CH₃ H Cl CO—N(CH₃)—CH₂—CO—OCH₃ Ia.360 CH₃ H Cl CO—N(CH₃)—CH₂—CO—OCH₂—CH═CH₂ Ia.361 CH₃ H Cl CO—N(CH₃)—CH₂—CO—OCH₂CH₂—OCH₃ Ia.362 CH₃ H Cl CO—N(CH₃)—CH(CH₃)—CO—OCH₃ Ia.363 CH₃ H Cl CO—N(CH₃)—CH(CH₃)—CO—OCH₂—CH═CH₂ Ia.364 CH₃ H Cl CO—N(CH₃)—CH(CH₃)—CO—OCH₂CH₂—OCH₃ Ia.365 CH₃ H Cl CH═C(Cl)—CO—OCH₂—CH═CH₂ Ia.366 CH₃ H Cl CH═C(Cl)—CO—OCH₂—C≡CH Ia.367 CH₃ H Cl CH═C(Cl)—CO—OCH₂—CO—OCH₃ Ia.368 CH₃ H Cl CH═C(Cl)—CO—OCH(CH₃)—CO—OCH₃ Ia.369 CH₃ H Cl CH═C(Cl)—CO—N(CH₃)—CH₂—CO—OCH₃ Ia.370 CH₃ H Cl CH═C(Cl)—CO—NH—CH(CH₃)—CO—OCH₃ Ia.371 CH₃ H CN OCH₃ Ia.372 CH₃ H CN OCH(CH₃)₂ Ia.373 CH₃ H CN O—CH₂—CH═CH₂ Ia.374 CH₃ H CN O-cyclopentyl Ia.375 CH₃ H CN OCH₂—CO—OCH₃ Ia.376 CH₃ H CN OCH₂—CO—OCH₂—CH═CH₂ Ia.377 CH₃ H CN OCH₂—CO—OCH₂—CH═CH—CH₃ Ia.378 CH₃ H CN OCH₂—CO—OCH₂CH₂—CH═CH₂ Ia.379 CH₃ H CN OCH₂—CO—OCH₂—CH═C(CH₃)₂ Ia.380 CH₃ H CN OCH₂—CO—OCH₂—C≡CH Ia.381 CH₃ H CN OCH₂—CO—OCH₂CH₂—C≡CH Ia.382 CH₃ H CN OCH₂—CO—O-cyclopentyl Ia.383 CH₃ H CN OCH₂—CO—O—CH₂CH₂—OCH₃ Ia.384 CH₃ H CN OCH₂—CO—O—CH₂CH₂—OC₂H₅ Ia.385 CH₃ H CN OCH₂—CO—OCH₂-cyclopropyl Ia.386 CH₃ H CN OCH₂—CO—OCH₂-cyclobutyl Ia.387 CH₃ H CN OCH₂—CO—OCH₂-cyclopentyl Ia.388 CH₃ H CN OCH₂—CO—OCH₂-cyclohexyl Ia.389 CH₃ H CN OCH₂—CO—NH—CH₃ Ia.390 CH₃ H CN OCH₂—CO—N(CH₃)₂ Ia.391 CH₃ H CN OCH(CH₃)—CO—OCH₂—CH═CH₂ Ia.392 CH₃ H CN OCH(CH₃)—CO—OCH₂—CH═CH—CH₃ Ia.393 CH₃ H CN OCH(CH₃)—CO—OCH₂CH₂—CH═CH₂ Ia.394 CH₃ H CN OCH(CH₃)—CO—OCH₂—CH═C(CH₃)₂ Ia.395 CH₃ H CN OCH(CH₃)—CO—OCH₂—C≡CH Ia.396 CH₃ H CN OCH(CH₃)—CO—OCH₂CH₂—C≡CH Ia.397 CH₃ H CN OCH(CH₃)—CO—O-cyclopentyl Ia.398 CH₃ H CN OCH(CH₃)—CO—OCH₂CH₂—OC₂H₅ Ia.399 CH₃ H CN OCH(CH₃)—CO—OCH₂-cyclopropyl Ia.400 CH₃ H CN OCH(CH₃)—CO—OCH₂-cyclobutyl Ia.401 CH₃ H CN OCH(CH₃)—CO—OCH₂-cyclopentyl Ia.402 CH₃ H CN OCH(CH₃)—CO—OCH₂-cyclohexyl Ia.403 CH₃ H CN OCH(CH₃)—CO—NH—CH₃ Ia.404 CH₃ H CN OCH(CH₃)—CO—N(CH₃)₂ Ia.405 CH₃ H CN OC(CH₃)₂—CO—OCH₃ Ia.406 CH₃ H CN OC(CH₃)₂—CO—OCH₂—CH═CH₂ Ia.407 CH₃ H CN OC(CH₃)₂—CO—OCH₂—C≡CH Ia.408 CH₃ H CN OC(CH₃)₂—CO—O-cyclopentyl Ia.409 CH₃ H CN OC(CH₃)₂—CO—OCH₂CH₂—OCH₃ Ia.410 CH₃ H CN COOH Ia.411 CH₃ H CN CO—OCH(CH₃)₂ Ia.412 CH₃ H CN CO—OCH₂—CH═CH₂ Ia.413 CH₃ H CN CO—OCH₂—C≡CH Ia.414 CH₃ H CN CO—O-cyclopentyl Ia.415 CH₃ H CN CO—OCH₂—CO—OCH₃ Ia.416 CH₃ H CN CO—OCH₂—CO—OCH₂—CH═CH₂ Ia.417 CH₃ H CN CO—OCH₂—CO—OCH₂—C≡CH Ia.418 CH₃ H CN CO—OCH₂—CO—OCH₂CH₂—OCH₃ Ia.419 CH₃ H CN CO—OCH(CH₃)—CO—OCH₂—C≡CH Ia.420 CH₃ H CN CO—CH(CH₃)—CO—OCH₂CH₂—OCH₃ Ia.421 CH₃ H CN CO—C(CH₃)₂—CO—OCH₂—C≡CH Ia.422 CH₃ H CN CO—C(CH₃)₂—CO—OCH₂CH₂—OCH₃ Ia.423 CH₃ H CN CO—NH—CH₂—CO—OCH₃ Ia.424 CH₃ H CN CO—NH—CH₂—CO—OCH₂—CH═CH₂ Ia.425 CH₃ H CN CO—NH—CH₂—CO—OCH₂CH₂—OCH₃ Ia.426 CH₃ H CN CO—NH—CH(CH₃)—CO—OCH₃ Ia.427 CH₃ H CN CO—NH—CH(CH₃)—CO—OCH₂—CH═CH₂ Ia.428 CH₃ H CN CO—NH—CH(CH₃)—CO—OCH₂CH₂—OCH₃ Ia.429 CH₃ H CN CO—N(CH₃)—CH₂—CO—OCH₃ Ia.430 CH₃ H CN CO—N(CH₃)—CH₂—CO—OCH₂—CH═CH₂ Ia.431 CH₃ H CN CO—N(CH₃)—CH₂—CO—OCH₂CH₂—OCH₃ Ia.432 CH₃ H CN CO—N(CH₃)—CH(CH₃)—CO—OCH₃ Ia.433 CH₃ H CN CO—N(CH₃)—CH(CH₃)—CO—OCH₂—CH═CH₂ Ia.434 CH₃ H CN CO—N(CH₃)—CH(CH₃)—CO—OCH₂CH₂—OCH₃ Ia.435 CH₃ H CN CH═C(Cl)—CO—OCH₂—CH═CH₂ Ia.436 CH₃ H CN CH═C(Cl)—CO—OCH₂—C≡CH Ia.437 CH₃ H CN CH═C(Cl)—CO—OCH₂—CO—OCH₃ Ia.438 CH₃ H CN CH═C(Cl)—CO—OCH(CH₃)—CO—OCH₃ Ia.439 CH₃ H CN CH═C(Cl)—CO—N(CH₃)—CH₂—CO—OCH₃ Ia.440 CH₃ H CN CH═C(Cl)—CO—NH—CH(CH₃)—CO—OCH₃ Ia.441 NH₂ F Cl OCH₃ Ia.442 NH₂ F Cl OCH(CH₃)₂ Ia.443 NH₂ F Cl OCH₂—CH═CH₂ Ia.444 NH₂ F Cl O-cyclopentyl Ia.445 NH₂ F Cl OCH₂—CO—OCH₃ Ia.446 NH₂ F Cl OCH₂—CO—OCH₂—CH═CH₂ Ia.447 NH₂ F Cl OCH₂—CO—OCH₂—CH═CH—CH₃ Ia.448 NH₂ F Cl OCH₂—CO—OCH₂CH₂—CH═CH₂ Ia.449 NH₂ F Cl OCH₂—CO—OCH₂—CH═C(CH₃)₂ Ia.450 NH₂ F Cl OCH₂—CO—OCH₂—C≡CH Ia.451 NH₂ F Cl OCH₂—CO—OCH₂CH₂—C≡CH Ia.452 NH₂ F Cl OCH₂—CO—O-cyclopentyl Ia.453 NH₂ F Cl OCH₂—CO—OCH₂CH₂—OCH₃ Ia.454 NH₂ F Cl OCH₂—CO—OCH₂CH₂—OC₂H₅ Ia.455 NH₂ F Cl OCH₂—CO—OCH₂-cyclopropyl Ia.456 NH₂ F Cl OCH₂—CO—OCH₂-cyclobutyl Ia.457 NH₂ F Cl OCH₂—CO—OCH₂-cyclopentyl Ia.458 NH₂ F Cl OCH₂—CO—OCH₂-cyclohexyl Ia.459 NH₂ F Cl OCH₂—CO—NH—CH₃ Ia.460 NH₂ F Cl OCH₂—CO—N(CH₃)₂ Ia.461 NH₂ F Cl OCH(CH₃)—CO—OCH₂—CH═CH₂ Ia.462 NH₂ F Cl OCH(CH₃)—CO—OCH₂—CH═CH—CH₃ Ia.463 NH₂ F Cl OCH(CH₃)—CO—OCH₂CH₂—CH═CH₂ Ia.464 NH₂ F Cl OCH(CH₃)—CO—OCH₂—CH═C(CH₃)₂ Ia.465 NH₂ F Cl OCH(CH₃)—CO—OCH₂—C≡CH Ia.466 NH₂ F Cl OCH(CH₃)—CO—OCH₂CH₂—C≡CH Ia.467 NH₂ F Cl OCH(CH₃)—CO—O-cyclopentyl Ia.468 NH₂ F Cl OCH(CH₃)—CO—OCH₂CH₂—OC₂H₅ Ia.469 NH₂ F Cl OCH(CH₃)—CO—OCH₂-cyclopropyl Ia.470 NH₂ F Cl OCH(CH₃)—CO—OCH₂-cyclobutyl Ia.471 NH₂ F Cl OCH(CH₃)—CO—OCH₂-cyclopentyl Ia.472 NH₂ F Cl OCH(CH₃)—CO—OCH₂-cyclohexyl Ia.473 NH₂ F Cl OCH(CH₃)—CO—NH—CH₃ Ia.474 NH₂ F Cl OCH(CH₃)—CO—N(CH₃)₂ Ia.475 NH₂ F Cl OC(CH₃)₂—CO—OCH₃ Ia.476 NH₂ F Cl OC(CH₃)₂—CO—OCH₂—CH═CH₂ Ia.477 NH₂ F Cl OC(CH₃)₂—CO—OCH₂—C≡CH Ia.478 NH₂ F Cl OC(CH₃)₂—CO—O-cyclopentyl Ia.479 NH₂ F Cl OC(CH₃)₂—CO—OCH₂CH₂—OCH₃ Ia.480 NH₂ F Cl COOH Ia.481 NH₂ F Cl CO—OCH(CH₃)₂ Ia.482 NH₂ F Cl CO—OCH₂—CH═CH₂ Ia.483 NH₂ F Cl CO—OCH₂—C≡CH Ia.484 NH₂ F Cl CO—O-cyclopentyl Ia.485 NH₂ F Cl CO—OCH₂—CO—OCH₃ Ia.486 NH₂ F Cl CO—OCH₂—CO—OCH₂—CH═CH₂ Ia.487 NH₂ F Cl CO—OCH₂—CO—OCH₂—C≡CH Ia.488 NH₂ F Cl CO—OCH₂—CO—OCH₂CH₂—OCH₃ Ia.489 NH₂ F Cl CO—OCH(CH₃)—CO—OCH₂—C≡CH Ia.490 NH₂ F Cl CO—OCH(CH₃)—CO—OCH₂CH₂—OCH₃ Ia.491 NH₂ F Cl CO—OC(CH₃)₂—CO—OCH₂—C≡CH Ia.492 NH₂ F Cl CO—OC(CH₃)₂—CO—OCH₂CH₂—OCH₃ Ia.493 NH₂ F Cl CO—NH—CH₂—CO—OCH₃ Ia.494 NH₂ F Cl CO—NH—CH₂—CO—OCH₂CH═CH₂ Ia.495 NH₂ F Cl CO—NH—CH₂—CO—OCH₂CH₂—OCH₃ Ia.496 NH₂ F Cl CO—NH—CH(CH₃)—CO—OCH₃ Ia.497 NH₂ F Cl CO—NH—CH(CH₃)—CO—OCH₂—CH═CH₂ Ia.498 NH₂ F Cl CO—NH—CH(CH₃)—CO—OCH₂CH₂—OCH₃ Ia.499 NH₂ F Cl CO—N(CH₃)—CH₂—CO—OCH₃ Ia.500 NH₂ F Cl CO—N(CH₃)—CH₂—CO—OCH₂—CH═CH₂ Ia.501 NH₂ F Cl CO—N(CH₃)—CH₂—CO—OCH₂CH₂—OCH₃ Ia.502 NH₂ F Cl CO—N(CH₃)—CH(CH₃)—CO—OCH₃ Ia.503 NH₂ F Cl CO—N(CH₃)—CH(CH₃)—CO—OCH₂—CH═CH₂ Ia.504 NH₂ F Cl CO—N(CH₃)—CH(CH₃)—CO—OCH₂CH₂—OCH₃ Ia.505 NH₂ F Cl CH═C(Cl)—CO—OCH₂—CH═CH₂ Ia.506 NH₂ F Cl CH═C(Cl)—CO—OCH₂—C≡CH Ia.507 NH₂ F Cl CH═C(Cl)—CO—OCH₂—CO—OCH₃ Ia.508 NH₂ F Cl CH═C(Cl)—CO—OCH(CH₃)—CO—OCH₃ Ia.509 NH₂ F Cl CH═C(Cl)—CO—N(CH₃)—CH₂—CO—OCH₃ Ia.510 NH₂ F Cl CH═C(Cl)—CO—NH—CH(CH₃)—CO—OCH₃ Ia.511 NH₂ F CN OCH₃ Ia.512 NH₂ F CN OCH(CH₃)₂ Ia.513 NH₂ F CN OCH₂—CH═CH₂ Ia.514 NH₂ F CN O-cyclopentyl Ia.515 NH₂ F CN OCH₂—CO—OCH₃ Ia.516 NH₂ F CN OCH₂—CO—OCH₂—CH═CH₂ Ia.517 NH₂ F CN OCH₂—CO—OCH₂—CH═CH—CH₃ Ia.518 NH₂ F CN OCH₂—CO—OCH₂CH₂—CH═CH₂ Ia.519 NH₂ F CN OCH₂—CO—OCH₂—CH═C(CH₃)₂ Ia.520 NH₂ F CN OCH₂—CO—OCH₂—C≡CH Ia.521 NH₂ F CN OCH₂—CO—OCH₂CH₂—C≡CH Ia.522 NH₂ F CN OCH₂—CO—O-cyclopentyl Ia.523 NH₂ F CN OCH₂—CO—OCH₂CH₂—OCH₃ Ia.524 NH₂ F CN OCH₂—CO—OCH₂CH₂—OC₂H₅ Ia.525 NH₂ F CN OCH₂—CO—OCH₂-cyclopropyl Ia.526 NH₂ F CN OCH₂—CO—OCH₂-cyclobutyl Ia.527 NH₂ F CN OCH₂—CO—OCH₂-cyclopentyl Ia.528 NH₂ F CN OCH₂—CO—OCH₂-cyclohexyl Ia.529 NH₂ F CN OCH₂—CO—NH—CH₃ Ia.530 NH₂ F CN OCH₂—CO—N(CH₃)₂ Ia.531 NH₂ F CN OCH(CH₃)—CO—OCH₂—CH═CH₂ Ia.532 NH₂ F CN OCH(CH₃)—CO—OCH₂—CH═CH—CH₃ Ia.533 NH₂ F CN OCH(CH₃)—CO—OCH₂CH₂—CH═CH₂ Ia.534 NH₂ F CN OCH(CH₃)—CO—OCH₂—CH═C(CH₃)₂ Ia.535 NH₂ F CN OCH(CH₃)—CO—OCH₂—C≡CH Ia.536 NH₂ F CN OCH(CH₃)—CO—OCH₂CH₂—C≡CH Ia.537 NH₂ F CN OCH(CH₃)—CO—O-cyclopentyl Ia.538 NH₂ F CN OCH(CH₃)—CO—OCH₂CH₂—OC₂H₅ Ia.539 NH₂ F CN OCH(CH₃)—CO—OCH₂-cyclopropyl Ia.540 NH₂ F CN OCH(CH₃)—CO—OCH₂-cyclobutyl Ia.541 NH₂ F CN OCH(CH₃)—CO—OCH₂-cyclopentyl Ia.542 NH₂ F CN OCH(CH₃)—CO—OCH₂-cyclohexyl Ia.543 NH₂ F CN OCH(CH₃)—CO—NH—CH₃ Ia.544 NH₂ F CN OCH(CH₃)—CO—N(CH₃)₂ Ia.545 NH₂ F CN OC(CH₃)₂—CO—OCH₃ Ia.546 NH₂ F CN OC(CH₃)₂—CO—OCH₂—CH═CH₂ Ia.547 NH₂ F CN OC(CH₃)₂—CO—OCH₂—C≡CH Ia.548 NH₂ F CN OC(CH₃)₂—CO—O-cyclopentyl Ia.549 NH₂ F CN OC(CH₃)₂—CO—OCH₂CH₂—OCH₃ Ia.550 NH₂ F CN COOH Ia.551 NH₂ F CN CO—OCH(CH₃)₂ Ia.552 NH₂ F CN CO—OCH₂—CH═CH₂ Ia.553 NH₂ F CN CO—OCH₂—C≡CH Ia.554 NH₂ F CN CO—O-cyclopentyl Ia.555 NH₂ F CN CO—OCH₂—CO—OCH₃ Ia.556 NH₂ F CN CO—OCH₂—CO—OCH₂—CH═CH₂ Ia.557 NH₂ F CN CO—OCH₂—CO—OCH₂—C≡CH Ia.558 NH₂ F CN CO—OCH₂—CO—OCH₂CH₂—OCH₃ Ia.559 NH₂ F CN CO—OCH(CH₃)—CO—OCH₂—C≡CH Ia.560 NH₂ F CN CO—OCH(CH₃)—CO—OCH₂CH₂—OCH₃ Ia.561 NH₂ F CN CO—OC(CH₃)₂—CO—OCH₂—C≡CH Ia.562 NH₂ F CN CO—OC(CH₃)₂—CO—OCH₂CH₂—OCH₃ Ia.563 NH₂ F CN CO—NH—CH₂CO—OCH₃ Ia.564 NH₂ F CN CO—NH—CH₂CO—OCH₂CH═CH₂ Ia.565 NH₂ F CN CO—NH—CH₂CO—OCH₂CH₂—OCH₃ Ia.566 NH₂ F CN CO—NH—CH(CH₃)—CO—OCH₃ Ia.567 NH₂ F CN CO—NH—CH(CH₃)—CO—OCH₂—CH═CH₂ Ia.568 NH₂ F CN CO—NH—CH(CH₃)—CO—OCH₂CH₂—OCH₃ Ia.569 NH₂ F CN CO—N(CH₃)—CH₂—CO—OCH₃ Ia.570 NH₂ F CN CO—N(CH₃)—CH₂—CO—OCH₂—CH═CH₂ Ia.571 NH₂ F CN CO—N(CH₃)—CH₂—CO—OCH₂CH₂—OCH₃ Ia.572 NH₂ F CN CO—N(CH₃)—CH(CH₃)—CO—OCH₃ Ia.573 NH₂ F CN CO—N(CH₃)—CH(CH₃)—CO—OCH₂—CH═CH₂ Ia.574 NH₂ F CN CO—N(CH₃)—CH(CH₃)—CO—OCH₂CH₂—OCH₃ Ia.575 NH₂ F CN CH═C(Cl)—CO—OCH₂—CH═CH₂ Ia.576 NH₂ F CN CH═C(Cl)—CO—OCH₂—C≡CH Ia.577 NH₂ F CN CH═C(Cl)—CO—OCH₂—CO—OCH₃ Ia.578 NH₂ F CN CH═C(Cl)—CO—OCH(CH₃)—CO—OCH₃ Ia.579 NH₂ F CN CH═C(Cl)—CO—N(CH₃)—CH₂—CO—OCH₃ Ia.580 NH₂ F CN CH═C(Cl)—CO—NH—CH(CH₃)—CO—OCH₃ Ia.581 NH₂ H Cl OCH₃ Ia.582 NH₂ H Cl OCH(CH₃)₂ Ia.583 NH₂ H Cl OCH₂—CH═CH₂ Ia.584 NH₂ H Cl O-cyclopentyl Ia.585 NH₂ H Cl OCH₂—CO—OCH₃ Ia.586 NH₂ H Cl OCH₂—CO—OCH₂—CH═CH₂ Ia.587 NH₂ H Cl OCH₂—CO—OCH₂—CH═CH—CH₃ Ia.588 NH₂ H Cl OCH₂—CO—OCH₂CH₂—CH═CH₂ Ia.589 NH₂ H Cl OCH₂—CO—OCH₂CH═C(CH₃)₂ Ia.590 NH₂ H Cl OCH₂—CO—OCH₂—C≡CH Ia.591 NH₂ H Cl OCH₂—CO—OCH₂CH₂—C≡CH Ia.592 NH₂ H Cl OCH₂—CO—O-cyclopentyl Ia.593 NH₂ H Cl OCH₂—CO—OCH₂CH₂—OCH₃ Ia.594 NH₂ H Cl OCH₂—CO—OCH₂CH₂—OC₂H₅ Ia.595 NH₂ H Cl OCH₂—CO—OCH₂-cyclopropyl Ia.596 NH₂ H Cl OCH₂—CO—OCH₂-cyclobutyl Ia.597 NH₂ H Cl OCH₂—CO—OCH₂-cyclopentyl Ia.598 NH₂ H Cl OCH₂—CO—OCH₂-cyclohexyl Ia.599 NH₂ H Cl OCH₂—CO—NH—CH₃ Ia.600 NH₂ H Cl OCH₂—CO—N(CH₃)₂ Ia.601 NH₂ H Cl OCH(CH₃)—CO—OCH₂—CH═CH₂ Ia.602 NH₂ H Cl OCH(CH₃)—CO—OCH₂—CH═CH—CH₃ Ia.603 NH₂ H Cl OCH(CH₃)—CO—OCH₂—CH₂—CH═CH₂ Ia.604 NH₂ H Cl OCH(CH₃)—CO—OCH₂—CH═C(CH₃)₂ Ia.605 NH₂ H Cl OCH(CH₃)—CO—OCH₂—C≡CH Ia.606 NH₂ H Cl OCH(CH₃)—CO—OCH₂CH₂—C≡CH Ia.607 NH₂ H Cl OCH(CH₃)—CO—O-cyclopentyl Ia.608 NH₂ H Cl OCH(CH₃)—CO—OCH₂CH₂—OC₂H₅ Ia.609 NH₂ H Cl OCH(CH₃)—CO—OCH₂-cyclopropyl Ia.610 NH₂ H Cl OCH(CH₃)—CO—OCH₂-cyclobutyl Ia.611 NH₂ H Cl OCH(CH₃)—CO—OCH₂-cyclopentyl Ia.612 NH₂ H Cl OCH(CH₃)—CO—OCH₂-cyclohexyl Ia.613 NH₂ H Cl OCH(CH₃)—CO—NH—CH₃ Ia.614 NH₂ H Cl OCH(CH₃)—CO—N(CH₃)₂ Ia.615 NH₂ H Cl OC(CH₃)₂—CO—OCH₃ Ia.616 NH₂ H Cl OC(CH₃)₂—CO—OCH₂—CH═CH₂ Ia.617 NH₂ H Cl OC(CH₃)₂—CO—OCH₂—C≡CH Ia.618 NH₂ H Cl OC(CH₃)₂—CO—O-cyclopentyl Ia.619 NH₂ H Cl OC(CH₃)₂—CO—OCH₂CH₂—OCH₃ Ia.620 NH₂ H Cl COOH Ia.621 NH₂ H Cl CO—OCH(CH₃)₂ Ia.622 NH₂ H Cl CO—OCH₂—CH═CH₂ Ia.623 NH₂ H Cl CO—OCH₂—C≡CH Ia.624 NH₂ H Cl CO—O-cyclopentyl Ia.625 NH₂ H Cl CO—OCH₂—CO—OCH₃ Ia.626 NH₂ H Cl CO—OCH₂—CO—OCH₂—CH═CH₂ Ia.627 NH₂ H Cl CO—OCH₂—CO—OCH₂—C≡CH Ia.628 NH₂ H Cl CO—OCH₂—CO—OCH₂CH₂—OCH₃ Ia.629 NH₂ H Cl CO—OCH(CH₃)—CO—OCH₂—C≡CH Ia.630 NH₂ H Cl CO—OCH(CH₃)—CO—OCH₂CH₂—OCH₃ Ia.631 NH₂ H Cl CO—OC(CH₃)₂—CO—OCH₂—C≡CH Ia.632 NH₂ H Cl CO—OC(CH₃)₂—CO—OCH₂CH₂—OCH₃ Ia.633 NH₂ H Cl CO—NH—CH₂—CO—OCH₃ Ia.634 NH₂ H Cl CO—NH—CH₂—CO—OCH₂—CH═CH₂ Ia.635 NH₂ H Cl CO—NH—CH₂—CO—OCH₂CH₂—OCH₃ Ia.636 NH₂ H Cl CO—NH—CH(CH₃)—CO—OCH₃ Ia.637 NH₂ H Cl CO—NH—CH(CH₃)—CO—OCH₂—CH═CH₂ Ia.638 NH₂ H Cl CO—NH—CH(CH₃)—CO—OCH₂CH₂—OCH₃ Ia.639 NH₂ H Cl CO—N(CH₃)—CH₂—CO—OCH₃ Ia.640 NH₂ H Cl CO—N(CH₃)—CH₂—CO—OCH₂—CH═CH₂ Ia.641 NH₂ H Cl CO—N(CH₃)—CH₂—CO—OCH₂CH₂—OCH₃ Ia.642 NH₂ H Cl CO—N(CH₃)—CH(CH₃)—CO—OCH₃ Ia.643 NH₂ H Cl CO—N(CH₃)—CH(CH₃)—CO—OCH₂—CH═CH₂ Ia.644 NH₂ H Cl CO—N(CH₃)—CH(CH₃)—CO—OCH₂CH₂—OCH₃ Ia.645 NH₂ H Cl CH═C(Cl)—CO—OCH₂—CH═CH₂ Ia.646 NH₂ H Cl CH═C(Cl)—CO—OCH₂—C≡CH Ia.647 NH₂ H Cl CH═C(Cl)—CO—OCH₂—CO—OCH₃ Ia.648 NH₂ H Cl CH═C(Cl)—CO—OCH(CH₃)—CO—OCH₃ Ia.649 NH₂ H Cl CH═C(Cl)—CO—N(CH₃)—CH₂—CO—OCH₃ Ia.650 NH₂ H Cl CH═C(Cl)—CO—NH—CH(CH₃)—CO—OCH₃ Ia.651 NH₂ H CN OCH₃ Ia.652 NH₂ H CN OCH(CH₃)₂ Ia.653 NH₂ H CN OCH₂—CH═CH₂ Ia.654 NH₂ H CN O-cyclopentyl Ia.655 NH₂ H CN OCH₂—CO—OCH₃ Ia.656 NH₂ H CN OCH₂—CO—OCH₂—CH═CH₂ Ia.657 NH₂ H CN OCH₂—CO—OCH₂—CH═CHCH₃ Ia.658 NH₂ H CN OCH₂—CO—OCH₂CH₂—CH═CH₂ Ia.659 NH₂ H CN OCH₂—CO—OCH₂—CH═C(CH₃)₂ Ia.660 NH₂ H CN OCH₂—CO—OCH₂—C≡CH Ia.661 NH₂ H CN OCH₂—CO—OCH₂CH₂—C≡CH Ia.662 NH₂ H CN OCH₂—CO—O-cyclopentyl Ia.663 NH₂ H CN OCH₂—CO—OCH₂CH₂—OCH₃ Ia.664 NH₂ H CN OCH₂—CO—OCH₂CH₂—OC₂H₅ Ia.665 NH₂ H CN OCH₂—CO—OCH₂-cyclopropyl Ia.666 NH₂ H CN OCH₂—CO—OCH₂-cyclobutyl Ia.667 NH₂ H CN OCH₂—CO—OCH₂-cyclopentyl Ia.668 NH₂ H CN OCH₂—CO—OCH₂-cyclohexyl Ia.669 NH₂ H CN OCH₂—CO—NH—CH₃ Ia.670 NH₂ H CN OCH₂—CO—N(CH₃)₂ Ia.671 NH₂ H CN OCH(CH₃)—CO—OCH₂—CH═CH₂ Ia.672 NH₂ H CN OCH(CH₃)—CO—OCH₂—CH═CH—CH₃ Ia.673 NH₂ H CN OCH(CH₃)—CO—OCH₂CH₂—CH═CH₂ Ia.674 NH₂ H CN OCH(CH₃)—CO—OCH₂—CH═C(CH₃)₂ Ia.675 NH₂ H CN OCH(CH₃)—CO—OCH₂—C≡CH Ia.676 NH₂ H CN OCH(CH₃)—CO—OCH₂CH₂—C≡CH Ia.677 NH₂ H CN OCH(CH₃)—CO—O-cyclopentyl Ia.678 NH₂ H CN OCH(CH₃)—CO—OCH₂CH₂—OC₂H₅ Ia.679 NH₂ H CN OCH(CH₃)—CO—OCH₂-cyclopropyl Ia.680 NH₂ H CN OCH(CH₃)—CO—OCH₂-cyclobutyl Ia.681 NH₂ H CN OCH(CH₃)—CO—OCH₂-cyclopentyl Ia.682 NH₂ H CN OCH(CH₃)—CO—OCH₂-cyclohexyl Ia.683 NH₂ H CN OCH(CH₃)—CO—NH—CH₃ Ia.684 NH₂ H CN OCH(CH₃)—CO—N(CH₃)₂ Ia.685 NH₂ H CN OC(CH₃)₂—CO—OCH₃ Ia.686 NH₂ H CN OC(CH₃)₂—CO—OCH₂—CH═CH₂ Ia.687 NH₂ H CN OC(CH₃)₂—CO—OCH₂—C≡CH Ia.688 NH₂ H CN OC(CH₃)₂—CO—O-cyclopentyl Ia.689 NH₂ H CN OC(CH₃)₂—CO—OCH₂CH₂—OCH₃ Ia.690 NH₂ H CN COOH Ia.691 NH₂ H CN CO—OCH(CH₃)₂ Ia.692 NH₂ H CN CO—OCH₂—CH═CH₂ Ia.693 NH₂ H CN CO—OCH₂—C≡CH Ia.694 NH₂ H CN CO—O-cyclopentyl Ia.695 NH₂ H CN CO—OCH₂—CO—OCH₃ Ia.696 NH₂ H CN CO—OCH₂—CO—OCH₂—CH═CH₂ Ia.697 NH₂ H CN CO—OCH₂—CO—OCH₂—C≡CH Ia.698 NH₂ H CN CO—OCH₂—CO—OCH₂CH₂—OCH₃ Ia.699 NH₂ H CN CO—OCH(CH₃)—CO—OCH₂—C≡CH Ia.700 NH₂ H CN CO—OCH(CH₃)—CO—OCH₂CH₂—OCH₃ Ia.701 NH₂ H CN CO—OC(CH₃)₂—CO—OCH₂—C≡CH Ia.702 NH₂ H CN CO—OC(CH₃)₂—CO—OCH₂CH₂—OCH₃ Ia.703 NH₂ H CN CO—NH—CH₂—CO—OCH₃ Ia.704 NH₂ H CN CO—NH—CH₂—CO—OCH₂—CH═CH₂ Ia.705 NH₂ H CN CO—NH—CH₂—CO—OCH₂CH₂—OCH₃ Ia.706 NH₂ H CN CO—NH—CH(CH₃)—CO—OCH₃ Ia.707 NH₂ H CN CO—NH—CH(CH₃)—CO—OCH₂—CH═CH₂ Ia.708 NH₂ H CN CO—NH—CH(CH₃)—CO—OCH₂CH₂—OCH₃ Ia.709 NH₂ H CN CO—N(CH₃)—CH₂—CO—OCH₃ Ia.710 NH₂ H CN CO—N(CH₃)—CH₂—CO—OCH₂—CH═CH₂ Ia.711 NH₂ H CN CO—N(CH₃)—CH₂—CO—OCH₂CH₂—OCH₃ Ia.712 NH₂ H CN CO—N(CH₃)—CH(CH₃)—CO—OCH₃ Ia.713 NH₂ H CN CO—N(CH₃)—CH(CH₃)—CO—OCH₂—CH═CH₂ Ia.714 NH₂ H CN CO—N(CH₃)—CH(CH₃)—CO—OCH₂CH₂—OCH₃ Ia.715 NH₂ H CN CH═C(Cl)—CO—OCH₂—CH═CH₂ Ia.716 NH₂ H CN CH═C(Cl)—CO—OCH₂—C≡CH Ia.717 NH₂ H CN CH═C(Cl)—CO—OCH₂—CO—OCH₃ Ia.718 NH₂ H CN CH═C(Cl)—CO—OCH(CH₃)—CO—OCH₃ Ia.719 NH₂ H CN CH═C(Cl)—CO—N(CH₃)—CH₂—CO—OCH₃ Ia.720 NH₂ H CN CH═C(Cl)—CO—NH—CH(CH₃)—CO—OCH₃

Other particularly preferred 1-aryl-4-thiotriazines are those of the formula Ib, in particular the compounds Ib.1 to Ib.720, which differ from the corresponding compounds Ia.1 to Ia.720 only by the fact that R² is amino:

Other particularly preferred 1-aryl-4-thiotriazines are those of the formula Ic {{circumflex over (=)} I where Y+R⁵=>C—O—C(R⁶)═N—}

in particular the compounds Ic.1 to Ic.55, which are listed in able 2 below:

TABLE 2 No. R¹ R² R³ R⁴ R⁶ Ic.1 CH₃ CH₃ H Cl H Ic.2 CH₃ CH₃ H Cl CH₃ Ic.3 CH₃ CH₃ H Cl C₂H₅ Ic.4 CH₃ CH₃ H Cl i-C₃H₇ Ic.5 CH₃ CH₃ H Cl cyclopropyl Ic.6 CH₃ CH₃ H Cl allyl Ic.7 CH₃ CH₃ H Cl propargyl Ic.8 CH₃ CH₃ H Cl 1-(methoxycarbo- nyl)ethyl Ic.9 CH₃ CH₃ H Cl OCH₃ Ic.10 CH₃ CH₃ H Cl OC₂H₅ Ic.11 CH₃ CH₃ H Cl O-i-C₃H₇ Ic.12 CH₃ CH₃ F Cl H Ic.13 CH₃ CH₃ F Cl CH₃ Ic.14 CH₃ CH₃ F Cl C₂H₅ Ic.15 CH₃ CH₃ F Cl i-C₃H₇ Ic.16 CH₃ CH₃ F Cl cyclopropyl Ic.17 CH₃ CH₃ F Cl allyl Ic.18 CH₃ CH₃ F Cl propargyl Ic.19 CH₃ CH₃ F Cl 1-(methoxycarbo- nyl)ethyl Ic.20 CH₃ CH₃ F Cl OCH₃ Ic.21 CH₃ CH₃ F Cl OC₂H₅ Ic.22 CH₃ CH₃ F Cl OCH(CH₃)₂ Ic.23 CH₃ CH₃ F CN H Ic.24 CH₃ CH₃ F CN CH₃ Ic.25 CH₃ CH₃ F CN C₂H₅ Ic.26 CH₃ CH₃ F CN i-C₃H₇ Ic.27 CH₃ CH₃ F CN cyclopropyl Ic.28 CH₃ CH₃ F CN allyl Ic.29 CH₃ CH₃ F CN propargyl Ic.30 CH₃ CH₃ F CN 1-(methoxycarbo- nyl)ethyl Ic.31 CH₃ CH₃ F CN OCH₃ Ic.32 CH₃ CH₃ F CN OC₂H₅ Ic.33 CH₃ CH₃ F CN OCH(CH₃)₂ Ic.34 CH₃ NH₂ Cl H Ic.35 CH₃ NH₂ Cl CH₃ Ic.36 CH₃ NH₂ Cl C₂H₅ Ic.37 CH₃ NH₂ Cl i-C₃H₇ Ic.38 CH₃ NH₂ Cl cyclopropyl Ic.39 CH₃ NH₂ Cl allyl Ic.40 CH₃ NH₂ Cl propargyl Ic.41 CH₃ NH₂ Cl 1-(methoxycarbo- nyl)ethyl Ic.42 CH₃ NH₂ Cl OCH₃ Ic.43 CH₃ NH₂ Cl OC₂H₅ Ic.44 CH₃ NH₂ Cl OCH(CH₃)₂ Ic.45 CH₃ NH₂ CN H Ic.46 CH₃ NH₂ CN CH₃ Ic.47 CH₃ NH₂ CN C₂H₅ Ic.48 CH₃ NH₂ CN i-C₃H₇ Ic.49 CH₃ NH₂ CN cyclopropyl Ic.50 CH₃ NH₂ CN allyl Ic.51 CH₃ NH₂ CN propargyl Ic.52 CH₃ NH₂ CN 1-(methoxycarbo- nyl)ethyl Ic.53 CH₃ NH₂ CN OCH₃ Ic.54 CH₃ NH₂ CN OC₂H₅ Ic.55 CH₃ NH₂ CN OCH(CH₃)₂

The 1-aryl-4-thiotriazines of the formula I can be obtained by various routes, in particular by one of the following processes:

A) Analogously to J. Chem. Soc. Perkin Trans. (1982), 1321

 As regards the conditions for carrying out the reaction, the abovementioned reference may be referred to.

B) Analogously to J. Chem. Soc. Perkin Trans. (1992), 1139

 As regards the reaction conditions, the abovementioned reference may be referred to.

In accordance with a preferred process, which constitutes a further subject matter of the invention, the 1-aryl-4-thiotriazines according to the invention are prepared by reacting aryl isocyanates with thioureas, followed by cyclization.

In accordance with an especially preferred embodiment of process C according to the invention, the isocyanate is reacted with the thiourea in the presence of an activated carbon dioxide source. Preferred examples which may be mentioned here are carbodiimidazole, phosgene, diphosgene and triphosgene, and chloroformic esters.

Process (C₎) according to the invention and processes (A₎) and (B₎) for the preparation of the compounds of the formula (I) are preferably carried out in the presence of a suitable reaction auxiliary.

Suitable reaction auxiliaries are generally the customary inorganic or organic bases or acid acceptors. These preferably include the acetates, amides, carbonates, hydrogen carbonates, hydrides, hydroxides or alkoxides of alkali metals or alkaline earth metals, for example sodium acetate, potassium acetate, calcium acetate, lithium amide, sodium amide, potassium amide, calcium amide, sodium carbonate, potassium carbonate, calcium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, calcium hydrogen carbonate, lithium hydride, sodium hydride, potassium hydride, calcium hydride, lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium methoxide, potassium methoxide, sodium ethoxide, potassium ethoxide, sodium n- or iso-propoxide, potassium n- or iso-propoxide, sodium n-, iso, sec- or tert-butoxide or potassium n-, iso-, sec- or tert-butoxide; furthermore also basic organic nitrogen compounds, for example trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N,N-dimethylcyclohexylamine, dicyclohexylamine, ethyldicyclohexylamine, N,N-dimethylaniline, N,N-dimethylbenzylamine, pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl- and 3,5-dimethylpyridine, 5-ethyl-2-methylpyridine, 4-dimethylaminopyridine, N-methylpiperidine, 1,4-diazabicyclo[2,2,2]octane (DABCO), 1,5-diazabicyclo[4,3,0]non-5-ene (DBN) or 1,8 diazabicyclo[5,4,0]undec-7-ene (DBU).

Process (C₎) according to the invention and processes (A₎) and (B₎) for the preparation of the compound of the formula (I) are preferably carried out in the presence of a diluent. Suitable diluents are, in general, the customary organic solvents. These preferably include aliphatic, alicyclic and aromatic unhalogenated or halogenated hydrocarbons, for example pentane, hexane, heptane, petroleum ether, ligroin, benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, cyclohexane, methylcyclohexane, dichloromethane (methylene chloride), trichloromethane (chloroform) or tetrachloromethane, dialkyl ethers such as diethyl ether, diisopropyl ether, methyl tert-butyl ether (MTBE), ethyl tert-butyl ether, methyl tert-pentyl ether (TAME), ethyl tert-pentyl ether, tetrahydrofuran (THF), 1,4-dioxane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether and diethylene glycol diethyl ether; dialkyl ketones such as acetone, butanone (methyl ethyl ketone), methyl isopropyl ketone and methyl isobutyl ketone; nitriles such as acetonitrile, propionitrile, butyronitrile and benzonitrile; amides such as N,N-dimethylformamide (DMF), N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone and hexamethylphosphoric triamide; esters such as methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate and sec-butyl acetate; sulfoxides such as dimethyl sulfoxide; alkanols such as methanol, ethanol, n-propanol, isopropanol, n-, iso-, sec- and tert-butanol; glycol ethers, such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether; mixtures of these with water, or pure water.

When carrying out processes (B₎) and (C₎), the reaction temperatures can be varied within a substantial range. In general, the process is carried out at temperatures from 0 to 200° C., preferably at 10 to 150° C., in particular at 20° C. to the boiling point of the reaction mixture in question.

To carry out processes (A₎), (B₎) and (C₎), the starting materials are generally employed in approximately equimolar amounts. However, it is also possible to employ in each case one of the components in a larger excess, approximately up to twice the molar amount of the other component.

Processes (A₎), (B₎) and (C₎) are expediently carried out under atmospheric pressure or under the inherent pressure of the reaction mixture in question. However, the processes may also be carried out under elevated or reduced pressure, in general at 0.1 to 10 bar.

The reaction mixtures in question are generally worked up by methods known per se, for example by diluting the reaction solution with water and subsequently isolating the product by means of filtration, crystallization or solvent extraction, or by removing the solvent, partitioning the residue in a mixture of water and a suitable organic solvent and working up the organic phase to arrive at the product.

In general, the 1-aryl-4-thiotriazines I can be prepared by one of the abovementioned synthetic processes. However, for economic or process engineering reasons, it may be more expedient to synthesize some compounds I from similar 1-aryl-4-thiotriazines—which, however, differ in particular with regard to the meanings of the radicals R⁵—, in a manner known per se, for example by hydrolysis, esterification, transesterification, amidation, acetalization, acetal hydrolysis, condensation reaction, Wittig reaction, Peterson olefination, etherification, alkylation, oxidation or reduction.

The preparation of the 1-aryl-4-thiotriazines I may lead to them being obtained as isomer mixtures; if desired, however, these can be resolved by the methods customary for this purpose, such as crystallization or chromatography, also on an optically active absorbate, to give the pure isomers. Pure optically active isomers can be synthesized advantageously from the corresponding optically active starting materials.

Agriculturally useful salts of the compounds I can be formed by reaction with a base of the cation in question, preferably an alkali metal hydroxide or alkali metal hydride, or by reaction with an acid of the anion in question, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

Salts of I whose metal ion is not an alkali metal ion can also be prepared in the customary manner by double decomposition of the alkali metal salt in question, and ammonium, phosphonium, sulfonium and sulfoxonium salts by means of ammonia, phosphonium hydroxide, sulfonium hydroxide or sulfoxonium hydroxide.

The compounds I and their agriculturally useful salts—as mixtures of isomers and also in the form of the pure isomers—are suitable for use as herbicides. The herbicidal compositions comprising I effect very good vegetation control on noncrop areas in particular at elevated rates of application. They effect very efficient control of broad-leaved weeds and grass weeds in crops such as wheat, rice, maize, soya and cotton without harming the crop plants to a significant extent. This effect is particularly pronounced at low rates of application.

Depending on the method of application in question, the compounds I, or herbicidal compositions comprising them, can also be employed in a further number of crop plants for eliminating undesirable plants. The following are examples of suitable crops:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

Moreover, the compounds I can also be employed in crops which have been rendered tolerant to the action of herbicides by means of breeding, including genetic engineering methods.

The compounds I, or the herbicidal compositions comprising them, can be used, for example, in the form of ready-to-spray aqueous solutions, powders, suspensions, also high-percentage aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for spreading or granules, by means of spraying, atomizing, dusting, spreading or pouring. The use forms depend on the intended aims; in any case, they should guarantee the finest possible distribution of the active ingredients according to the invention.

Suitable inert auxiliaries are essentially: mineral oil fractions of medium to high boiling point, such as kerosene and diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols, such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones, such as cyclohexanone, strongly polar solvents, e.g. amines, such as N-methylpyrrolidone, and water.

Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water. To prepare emulsions, pastes or oil dispersions, the 1-aryl-4-thiotriazines I, either as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetting agent, tackifier, dispersant or emulsifier. Alternatively, it is possible to prepare concentrates comprising active ingredient, wetting agent, tackifier, dispersant or emulsifier and, if desired, solvent or oil, which are suitable for dilution with water.

Suitable surfactants are the alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids, e.g. ligno-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl- and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols, and also of fatty alcohol glycol ethers, condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of naphthalene or of the naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl polyglycol ether, tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignosulfite waste liquors or methylcellulose.

Powders, materials for spreading and dusts can be prepared by mixing or grinding the active ingredients together with a solid carrier.

Granules, e.g. coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers. Solid carriers are mineral earths, such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders, or other solid carriers.

The concentrations of the active ingredients I in the ready-to-use products can be varied within wide ranges. In general, the formulations comprise from about 0.001 to 98% by weight, preferably 0.01 to 95% by weight, of at least one active ingredient. The active ingredients are employed in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum).

The following formulation examples illustrate the preparation of such products:

I. 20 parts by weight of compound No. 3 are dissolved in a mixture composed of 80 parts by weight of alkylated benzene, 10 parts by weight of the adduct of 8 to 10 mol of ethylene oxide to 1 mol of oleic acid N-monoethanolamide, 5 parts by weight of calcium dodecylbenzenesulfonate and 5 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active ingredient.

II. 20 parts by weight of compound No. 5 are dissolved in a mixture composed of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxide to 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active ingredient.

III. 20 parts by weight of active ingredient No. 12 are dissolved in a mixture composed of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction of boiling point 210 to 280° C. and 10 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active ingredient.

IV. 20 parts by weight of active ingredient No. 32 are mixed thoroughly with 3 parts by weight of sodium diisobutylnaphthalene-α-sulfonate, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of pulverulent silica gel, and the mixture is ground in a hammer mill. Finely distributing the mixture in 20,000 parts by weight of water gives a spray mixture comprising 0.1% by weight of the active ingredient.

V. 3 parts by weight of active ingredient No. 36 are mixed with 97 parts by weight of finely divided kaolin. This gives a dust comprising 3% by weight of the active ingredient.

VI. 20 parts by weight of active ingredient No. 41 are mixed intimately with 2 parts by weight of calcium dodecylbenzenesulfonate, 8 parts by weight of fatty alcohol polyglycol ether, 2 parts by weight of the sodium salt of a phenol/urea/formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil. This gives a stable oily dispersion.

VII. 1 part by weight of the compound No. 42 is dissolved in a mixture composed of 70 parts by weight of cyclohexanone, 20 parts by weight of ethoxylated isooctylphenol and 10 parts by weight of ethoxylated castor oil. This gives a stable emulsion concentrate.

VIII. 1 part by weight of the compound No. 64 is dissolved in a mixture composed of 80 parts by weight of cyclohexanone and 20 parts by weight of Wettol® EM 31 (=nonionic emulsifier based on ethoxylated castor oil; BASF AG). This gives a stable emulsion concentrate.

The active ingredients I or the herbicidal compositions can be applied pre- or post-emergence. If the active ingredients are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that they come into contact as little as possible, if at all, with the leaves of the sensitive crop plants, while the active ingredients reach the leaves of undesirable plants growing underneath, or the naked soil surface (post-directed, lay-by).

The application rates of active ingredient I are from 0.001 to 3.0, preferably 0.01 to 1.0, kg of active ingredient (a.i.) per ha, depending on the control target, the season, the target plants and the growth stage.

To widen the spectrum of action and to achieve synergistic effects, the 1-aryl-4-thiotriazines I may be mixed with a large number of representatives of other groups of herbicidal or growth-regulating active ingredients and then applied concomitantly. Suitable components for mixtures are, for example, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acid and its derivatives, aminotriazoles, anilides, aryloxy-/hetaryloxyalkanoic acids and their derivatives, benzoic acid and its derivatives, benzothiadiazinones, 2-(hetaroyl/aroyl)-1,3-cyclohexanediones, hetaryl aryl ketones, benzylisoxazolidinones, meta-CF₃-phenyl derivatives, carbamates, quinolin carboxylic acid and its derivatives, chloroacetanilides, cyclohexane-1,3-dione derivatives, diazines, dichloropropionic acid and its derivatives, dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy- and hetaryloxyphenoxypropionic esters, phenylacetic acid and its derivatives, 2-phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and its derivatives, pyrimidyl ethers, sulfonamides, sulfonyl ureas, triazines, triazinones, triazolinones, triazolcarboxamides and uracils.

Furthermore, it may be advantageous to apply the compounds I, alone or in combination with other herbicides, together as a mixture with further crop protection agents, for example with pesticides or agents for controlling phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions which are employed for treating nutrient and trace element deficiencies. Nonphytotoxic oils and oil concentrates may also be added.

PREPARATION EXAMPLE Example 1 Compound No. 38 3-(2,4-difluorophenyl)-1,5-dimethyl-6-thioxo-[1,3,5]triazinane-2,4-dione

31 g of 2,4-difluorophenyl isocyanate and 64.9 g of carbodiimidazole were added in succession to 20.8 g of N,N′-dimethylthiourea in 500 ml of toluene and 1 ml of triethylamine. This mixture was stirred first for 3 hours at 60-65° C. and then for 12 hours at 80-85° C. After cooling to room temperature, the mixture was washed three times with 100-ml-portions of water, and the organic phase was dried over sodium sulfate. After distillation of the low-boiling fractions, 48 g of the desired product of melting point 156-159° C. remained.

Example 2 Compound No. 40 2-Chloro-5-(3,5-dimethyl-2,6-dioxo-4-thioxo-[1,3,5]triazinan-1-yl)-benzaldehyde O-ethyl oxime

2.8 g of 3-ethoxyiminoethyl-4-chlorophenyl isocyanate and 4 g of carbodiimidazole were added in succession to 1.3 g of N,N′-dimethylurea in 20 ml of toluene and 0.4 ml of triethylamine. This mixture was stirred first for 2 hours at 60° C and then for 4 hours at 80° C. After cooling to room temperature, the mixture was washed four times with 20-ml-portions of water, and the organic phase was dried over sodium sulfate. The residue which remained after the solvent had been distilled off was purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate). Yield: 2.02 g; m.p.: 139-141° C.

Example 3 Compound No. 1 3-(4-Chloro-2-fluoro-5-hydroxyphenyl)-1,5-dimethyl-6-thioxo-[1,3,5]triazinane-2,4-dione

3 ml of triethylamine and then a solution of 22.4 g (91.2 mmol) of 4-chloro-2-fluoro-5-(methoxycarbonyloxy)phenyl isocyanate in 100 ml of toluene were added dropwise at approximately 20° C. to a solution of 9.5 g (91.2 mmol) of N,N′-dimethylthiourea in 20 ml of toluene. After addition of 29.6 g (182.5 mmol) of carbodiimidazole, the mixture was heated for 3 hours at 80° C. The reaction mixture was stirred overnight at approximately 20° C., then washed three times with water and finally concentrated under reduced pressure. The crude product was purified by column chromatography (mobile phase: cyclohexane/ethyl acetate=10:1). Yield: 18.1 g (63%); m.p.: 242-246° C.

Example 4 Compound No. 11 Allyl 2-[2-chloro-5-(3,5-dimethyl-2,6-dioxo-[1,3,5]triazinan-1-yl)-4-fluorophenoxy]propionate (racemate)

0.37 g (2.65 mmol) of K₂CO₃ and 0.51 g (2.65 mmol) of rac. allyl 2-bromopropionate were added approximately at 20° C. to a solution of 0.80 g (2.52 mmol) of 3-(4-chloro-2-fluoro-5-hydroxyphenyl)-1,5-dimethyl-6-thioxo-[1,3,5]triazinane-2,4-dione in 15 ml of dimethylformamide. After the reaction mixture had been stirred for two hours at approximately 20° C., it was stirred into ice-water. The product was extracted three times with methyl tert-butyl ether. The combined organic phases were dried over magnesium sulfate and then concentrated. The crude product (1.18 g) was purified by column chromatography (mobile phase: cyclohexane/ethyl acetate=15:1). Yield: 0.88 g (81%); ¹H NMR (270 MHz, in CDCl₃): δ[ppm]=1.7 (d, 3H), 3.8 (s, 6H), 4.6 (m, 2H), 4.7 (q, 1H), 5.2 (d, 1H), 5.3 (d, 1H), 5.9 (m, 1H), 6.9 (d, 1H), 7.3 (d, 1H).

Example 5 Compound No. 12 Allyl (R)-2-[2-chloro-5-(3,5-dimethyl-2,6-dioxo-[1,3,5]triazinan-1-yl)-4-fluorophenoxy]propionate (R isomer)

0.38 g (1.89 mmol) of diisopropyl azodicarboxylate was added dropwise at 0° C. in the course of 5 minutes to a solution of 0.50 g (1.58 mmol) of 3-(4-chloro-2-fluoro-5-hydroxyphenyl)-1,5-dimethyl-6-thioxo-[1,3,5]triazinane-2,4-dione, 0.20 g (1.58 mmol) of allyl S-lactate and 0.48 g (1.81 mmol) of triphenylphosphine. Then, the mixture was stirred for 2 hours at 0-5° C., whereupon the reaction mixture was concentrated under reduced pressure. The crude product was taken up in methylene chloride. The resulting solution was washed twice with water, then dried over magnesium sulfate and finally concentrated. The crude product (1.88 g) was purified by column chromatography (mobile phase: cyclohexane/ethyl acetate=9:1). Yield: 0.64 g (94%); ¹H NMR see Example 4.

Example 6 Compound No. 24 Cyclobutylmethyl (R)-2-[2-chloro-5-(3,5-dimethyl-2,6-dioxo-4-thioxo-[1,3,5]triazinan-1-yl)-4-fluorophenoxy]propionate (R isomer)

36 mg (0.125 mmol, 10 mol%) of Ti[OCH(CH₃)₂]₄ were added to a solution of 504 mg (1.25 mmol) of methyl (R)-2-[2-chloro-5-(3,5-dimethyl-2,6-dioxo-[1,3,5]triazinan-1-yl)-4-fluorophenoxy]-propionate in 10 ml of cyclobutylmethanol. The resulting mixture was heated for 5 hours at reflux temperature, whereupon the reaction mixture was poured into ice-water. The product of value which had formed was extracted with ethyl acetate (4 times). The combined organic phases were subsequently dried over magnesium sulfate and then concentrated. The resulting crude product was purified by column chromatography (mobile phase: cyclohexane/ethyl acetate=25:1). Yield: 410 mg (72%);

¹H NMR (400 MHz, in CDCl₃): δ[ppm]=1.7 (d, 3H), 1.7 (m, 2H), 1.85 (m, 2H), 2.0 (m, 2H), 2.6 (quint., 1H), 3.8 (2s, je 3H), 4.1 (m, 2H), 4.7 (q, 1H), 6.9 (d, 1H), 7.35 (d, 1H).

Example 7 Compound No. 28 2-Chloro-5-(3,5-dimethyl-2,6-dioxo-4-thioxo-[1,3,5]triazinan-1-yl)-4-fluorobenzoic acid

Method A:

4.98 g (12.9 mmol) of isopropyl 2-chloro-5-(3,5-dimethyl-2,6-dioxo-4-thioxo-[1,3,5]triazinan-1-yl)-4-fluorobenzoate and 25 ml of concentrated sulfuric acid were heated for 7 hours at 80° C. Then, the reaction mixture was carefully poured into ice-water. The solid fraction which had formed was separated off and washed with water until neutral. After drying, 2.62 g (59%) of the desired acid were obtained; m.p. 225-229° C.

Method B:

108 mg (0.30 mmol) of methyl 2-chloro-5-(3,5-dimethyl-2,6-dioxo-4-thioxo-[1,3,5]triazinan-1-yl)-4-fluorobenzoate and 150 mg (0.75 mmol) of iodotrimethylsilane were heated for 2 hours at 100° C. After cooling, methyl tert-butyl ether and saturated aqueous sodium hydrogen carbonate solution were added to the reaction mixture (to pH 8). The aqueous phase was subsequently separated off and acidified with 10% strength hydrochloric acid (pH 5). It was then extracted three times with methylene chloride. The combined methylene chloride phases were then dried over magnesium sulfate and finally concentrated. Yield: 70 mg (67%); m.p. 225-229° C.

In Table 3 which follows, other 1-aryl-4-thiotriazines of the formula I which were, or can be, prepared in a similar manner are listed in addition to the active ingredients described above:

TABLE 3

No. R³ R⁴ R⁵ M.p. or HPLC/MS*⁾ 1 F Cl OH 242-246° C. 2 F Cl OCH₃ oil 3 F Cl OCH₂—C≡CH 178-180° C. 4 F Cl OCH(CH₃)—C≡CH oil 5 F Cl OCH(CH₃)₂ oil 6 F Cl O-Cyclopentyl 118-121° C. 7 F Cl OCH₂—CO—OCH₃ oil 8 F Cl OCH₂—CO—OCH₂—CH═CH₂ oil 9 F Cl OCH(CH₃)—CO—OCH₃ (rac.) oil 10 F Cl OCH(CH₃)—CO—OCH₃ (R) oil 11 F Cl OCH(CH₃)—CO—OCH₂—CH═CH₂ (rac.) oil 12 F Cl OCH(CH₃)—CO—OCH₂—CH═CH₂ (R) oil 13 F Cl OCH(CH₃)—CO—OCH₂—CH═CHCH₃ (R) oil 14 F Cl OCH(CH₃)—CO—OCH₂CH₂—CH═CH₂ (R) oil 15 F Cl OCH(CH₃)—CO—OCH₂—CH═C(CH₃)₂ (R) oil 16 F Cl OCH(CH₃)—CO—OCH₂—C≡CH (rac.) oil 17 F Cl OCH(CH₃)—CO—OCH₂—C≡CH (R) oil 18 F Cl OCH(CH₃)—CO—OCH₂CH₂—C≡CH (R) oil 19 F Cl OCH(CH₃)—CO—O-Cyclopentyl (R) 85-86° C. 20 F Cl OCH(CH₃)—CO—OCH₂CH₂—OCH₃ (rac.) oil 21 F Cl OCH(CH₃)—CO—OCH₂CH₂—OCH₃ (R) oil 22 F Cl OCH(CH₃)—CO—OCH₂CH₂—OC₂H₅ (R) oil 23 F Cl OCH(CH₃)—CO—OCH₂-Cyclopropyl (R) oil 24 F Cl OCH(CH₃)—CO—OCH₂-Cyclobutyl (R) oil 25 F Cl OCH(CH₃)—CO—NH—CH₃ (R) 150-154° C. 26 F Cl OCH(CH₃)—CO—N(CH₃)₂ (R) oil 27 F Cl OC(CH₃)₂—CO—OCH₂—CH═CH₂ oil 28 F Cl COOH 225-229° C. 29 F Cl CO—OCH(CH₃)₂ oil 30 F Cl CO—OCH₂—CH═CH₂ oil 31 F Cl CHO 136-139° C. 32 F Cl CH═N—OCH₃ 156-160° C. 33 F Cl CH═C(Cl)—CO—OC₂H₅ 177-182° C. 34 F CN F 180-184° C. 35 F CN OH 252-255° C. 36 F CN OCH₃ 208-210° C. 37 F CN OCH(CH₃)—CO—OCH₃ (rac.) 165-168° C. 38 F F H 156-159° C. 39 H Cl H 202-205° C. 40 H Cl CH═N—OC₂H₅ 139-141° C. 41 H Cl CO—OCH(CH₃)₂ 132-136° C. 42 H Cl CH═C(Cl)—CO—OC₂H₅ 212-218° C. 43 H Cl CH═C(Cl)—CO—OCH₂—CH═CH₂ 171-173° C. 44 F Cl OCH₂—CO—CH₃ M = 374, t = 3.91 45 F Cl OCH₂—CO—C(CH₃)₃ M = 416, t = 5.07 46 F Cl OCH₂—CO-cyclopropyl M = 400, t = 4.17 47 F Cl OCH₂—CO-phenyl M = 436, t = 5.07 48 F Cl OCH₂—CO-(4-fluorophenyl) M = 454, t = 4.45 49 F Cl OCH₂—CO-(4-chlorophenyl) M = 470, t = 5.24 50 F Cl OCH₂—CO-(4-bromophenyl) M = 515, t = 4.70 51 F Cl OCH₂—CO-(4-cyanophenyl) M = 461, t = 5.01 52 F Cl OCH₂—CO-(4-methoxyphenyl) M = 466, t = 5.09 53 F Cl OCH₂—CO-(4-nitrophenyl) M = 481, t = 5.08 54 F Cl OCH₂—CO-(2-nitrophenyl) M = 481, t = 4.39 55 F Cl OCH₂—CO-(3-nitrophenyl) M = 481, t = 4.40 56 F Cl OCH₂—CO-(3-methoxyphenyl) M = 466, t = 4.46 57 F Cl OCH₂—CO-(2,4-dichlorophenyl) M = 505, t = 4.82 58 F Cl OCH₂—CO-(2,4-dibromophenyl) M = 594, t = 4.88 59 F Cl OCH₂—CO-(2,4-dimethoxyphenyl) M = 496, t = 4.52 60 F Cl OCH₂—CO-(3,4-dichlorophenyl) M = 505, t = 4.83 61 F Cl OCH₂—CO-(2,3,4-trichlorophenyl) M = 539, t = 4.97 62 F Cl OCH₂—CO-(2,4-dichloro-3-methyl- M = 519, t = 4.97 phenyl) 63 F Cl OCH(CH₃)—CO-phenyl (rac.) M = 450, t = 4.58 *⁾HPLC/MS conditions: column GROM-SIL 80, ODS-7 pH, 4 μm, 40 × 2 mm; flow rate 0.7 ml/min, UV detector

Example 8 Compound No. 64 3(4-Chloro-2-cyclopropyl-6-fluorobenzoxazol-7-yl)-1,5-dimethyl-6-thioxo-[1,3,5]triazinane-2,4-dione (R⁶=cyclopropyl)

A mixture of 370 mg (1.11 mmol) of 3-(3-amino-4-chloro-6-fluoro-2-hydroxyphenyl)-1,5-dimethyl-6-thioxo-[1,3,5]triazinane-2,4-dione and 226 mg (1.67 mmol) of imidomethyl cyclopropanate hydrochloride in 20 ml of methanol (distilled off over Na) was stirred for 2 hours at approximately 20° C. The mixture was subsequently concentrated. The residue was slaked in water, whereupon the undissolved components were separated off and dissolved in ethyl acetate. The ester phase was dried over magnesium sulfate and then concentrated under reduced pressure. This gave 160 mg of crude product which was purified by column chromatography (mobile phase: cyclohexane/ethyl acetate=20:1). Yield: 90 mg (21%); oil;

¹H NMR (400 MHz, in CDCl₃): δ[ppm]=1.2-1.35 (m, 4H), 2.2 (m, 1H), 3.8 (s, 6H), 7.15 (d, 1H).

Precursor 8α 3-(3-Amino-4-chloro-6-fluoro-2-hydroxyphenyl)-1,5-dimethyl-6-thioxo-[1,3,5]triazinane-2,4-dione

0.46 g (1.33 mmol) of 3-(3-amino-4-chloro-6-fluoro-2-methoxyphenyl)-1,3-dimethyl-6-thioxo-[1,3,5]triazinane-2,4-dione in 5 ml of methylene chloride was added dropwise at 0° C. to 8 ml of a 1M solution of boron tribromide in methylene chloride (=8 mmol BBr₃). The reaction mixture was subsequently stirred for two hours at 0° C., whereupon it was slowly stirred into ice-water. The product of value was extracted from the aqueous phase using methylene chloride (twice). The combined organic phases were dried over magnesium sulfate and then concentrated under reduced pressure. This gave 0.21 g (48%) of the product of value.

The aqueous phase was brought to pH 10 using sodium hydroxide solution. Then, the mixture was reextracted with methylene chloride. Again, the methylene chloride phases were dried over magnesium sulfate and concentrated. This gave a further 0.16 g (36%) of the product of value.

Overall yield: 84%;

¹H NMR (270 MHz, in CDCl₃): δ[ppm]=3.8 (s, 6H), 6.9 (d, 1H).

Precursor 8β 3-(3-Amino-4-chloro-6-fluoro-2-methoxyphenyl)-1,3-dimethyl-6-thioxo-[1,3,5]triazinane-2,4-dione

A mixture of 0.22 g (3.98 mmol) of iron powder and 2.5 ml of acetic acid in 5 ml of methanol was heated at reflux temperature. At this temperature, a suspension of 0.50 g (1.33 mmol) of 3-(4-chloro-6-fluoro-2-methoxy-3-nitrophenyl)-1,5-dimethyl-6-thioxo-[1,3,5]triazinane-2,4-dione in 3 ml of methanol was slowly added dropwise to the reaction mixture. The mixture was subsequently stirred for two hours at reflux temperature. After the reaction mixture had been cooled and concentrated, the crude product was filtered over silica gel (mobile phase: ethyl acetate). The filtrate was concentrated under reduced pressure. After drying, 0.45 g (98%) of the product of value were obtained;

¹H NMR (400 MHz, in CDCl₃): δ[ppm]=3.75 (s, 3H), 3.8 (s, 6H), 4.05 (bs, 2H), 7.05 (d, 1H).

Precursor 8γ 3-(4-Chloro-6-fluoro-2-methoxy-3-nitrophenyl)-1,5-dimethyl-6-thioxo-[1,3,5]triazinane-2,4-dione

A solution of 3.0 g (15.0 mmol) of diphosgene in 5 ml of toluene was added dropwise at approximately 20° C. to a solution of 3.0 g (13.6 mmol) of 4-chloro-6-fluoro-2-methoxy-3-nitrophenylamine in 15 ml of toluene. Then, the mixture was slowly heated to reflux temperature and stirred for 6 hours under reflux. After the reaction mixture had been concentrated and dried, the crude isocyanate was redissolved in 5 ml of toluene to be used in the next reaction. 6 ml of triethylamine and a solution of 3.55 g (14.4 mmol) of dimethylthiourea were added dropwise to this solution at approximately 20° C. 4.7 g (28.8 mmol) of carbonyldiimidazole were subsequently added to the reaction mixture. The mixture was heated at 80° C. for 5 hours and then allowed to cool. For work-up, it was firstly washed four times with water. Then, the organic phase was dried over magnesium sulfate and concentrated under reduced pressure. The crude product (6.58 g) was purified by silica gel chromatography (mobile phase: cyclohexane/ethyl acetate=10:1). Yield: 1.31 g (24%);

¹H NMR (270 MHz, in CDCl₃): δ[ppm]=3.8 (s, 6H), 3.9 (s, 3H), 7.2 (d, 1H).

Precursor 8δ 4-Chloro-6-fluoro-2-methoxy-3-nitrophenylamine

A suspension of 40.0 g (152 mmol) of N-(4-chloro-6-fluoro-2-methoxy-3-nitrophenyl)acetamide in 800 ml of 6M hydrochloric acid was heated for 5 hours at reflux temperature, whereupon the mixture was stirred overnight at approximately 20° C. For work-up, the reaction mixture was stirred into ice-water. The pH was brought to 8-9 by adding sodium solution. The mixture was subsequently extracted six times with ethyl acetate. The combined organic phases were dried over magnesium sulfate and then concentrated under reduced pressure. Yield: 33 g (98%);

¹H NMR (270 MHz, in CDCl₃): δ[ppm]=3.9 (s, 3H), 4.0 (bs, 2H), 7.0 (d, 1H).

Precursor 8ε N-(4-Chloro-6-fluoro-2-methoxy-3-nitrophenyl)acetamide

A solution of 72.5 g (647 mmol) of NaOSi(CH₃)₃ in 25 ml of tetrahydrofuran was added dropwise at approximately 20° C. to a solution of 81 g (323 mmol) of N-(4-chloro-2,6-difluoro-3-nitro-phenyl)acetamide in 490 ml of dioxane and 50 ml of methanol. The mixture was subsequently heated for two hours at reflux temperature. After cooling and concentrating, the crude product (black oil) was stirred into ice-cold 10% strength hydrochloric acid. The resulting product of value was then extracted with ethyl acetate (3 times). The combined organic phases were dried over magnesium sulfate and concentrated under reduced pressure. The residue was stirred once with water. The insoluble components were removed and washed three times with water. After drying, 52.1 g (63%) of the product of value were obtained.

¹H NMR (270 MHz, in d⁶ dimethyl sulfoxide): δ[ppm]=2.1 (s, 3H), 3.85 (s, 3H), 7.75 (d, 1H), 9.9 (bs, 1H).

Precursor 8ζ N-(4-Chloro-2,6-difluoro-3-nitrophenyl)acetamide

30.7 g (487 mmol) of concentrated nitric acid were added dropwise at 0-5° C. to a solution of 100 g (487 mmol) of N-(4-chloro-2,6-difluorophenyl)acetamide in 500 ml of concentrated sulfuric acid. After the reaction mixture had been stirred for one hour at 0-5° C., it was stirred into ice-water. The resulting solid was separated off, washed twice with water and dried. Yield: 81.3 g (72%);

¹H NMR (270 MHz, in d⁶ dimethyl sulfoxide): δ[ppm]=2.1 (s, 3H), 7.95 (dd, 1H), 10.2 (bs, 1H).

Precursor 8θ N-(4-Chloro-2,6-difluorophenyl)acetamide

126 g (930 mmol) of sulfuryl chloride were added dropwise at 80° C. to a solution of 100 g (775 mmol) of difluoroaniline in 700 ml of glacial acetic acid. The mixture was subsequently stirred for three hours at 100° C. After cooling and concentration, the residue was treated with 200 ml of acetic anhydride. The mixture was then stirred overnight at approximately 20° C. For work-up, the reaction mixture was stirred into 1.5 l of ice-water. The product of value was extracted from the aqueous phase using ethyl acetate (3 times). The combined organic phases were dried over magnesium sulfate and concentrated under reduced pressure. Yield: 163 g;

¹H NMR (270 MHz, in d⁶ dimethyl sulfoxide): δ[ppm]=2.05 (s, 3H), 7.4 (d, 2H), 9.8 (bs, 1H).

The following were prepared similarly:

Compound No. 65 3-(4-chloro-6-fluorobenzoxazol-7-yl)-1,5-dimethyl-6-thioxo-[1,3,5]triazinane-2,4-dione (R⁶ =H; m.p.: 209-211° C.) and Compound No. 66 3-(4-chloro-2-ethyl-6-fluorobenzoxazol-7-yl)-1,5-dimethyl-6-thioxo-[1,3,5]triazinane-2,4-dione (R⁶=C₂H₅; m.p.: 156-159° C.). Example 9 Compound No. 67 3-(4-Chloro-6-fluorobenzoxazol-7-yl)-1,5-dimethyl-6-thioxo-[1,3,5]triazinane-2,4-dione (R⁶=hydrogen)

5.0 g (48.1 mmol) of trimethylformamide were added dropwise to a solution of 502 mg (1.50 mmol) of 3-(3-amino-4-chloro-6-fluoro-2-hydroxyphenyl)-1,5-dimethyl-6-thioxo-[1,3,5]-triazinane-2,4-dione in 10 ml of methanol. The mixture was then heated at reflux temperature for 9 hours. The reaction mixture was subsequently concentrated under reduced pressure. The resulting crude product was purified by means of column chromatography (mobile phase: cyclohexane/ethyl acetate=20:1). Yield: 240 mg (46%); m.p.: 209-211° C.

Compound No. 68

3-(4-chloro-2-ethyl-6-fluorobenzoxazol-7-yl)-1,5-dimethyl-6-thioxo-[1,3,5]triazinane-2,4-dione (R⁶=ethyl) was prepared in a similar manner.

Use Examples

The herbicidal action of 1-aryl-4-thiotriazines I was demonstrated by the following greenhouse experiments:

The culture vessels used were plastic flower pots containing, as substrate, loamy sand with approximately 3.0% humus. The seeds of the test plants were sown separately for each species.

For the pre-emergence treatment, the active ingredients which were suspended or emulsified in water were applied directly after sowing using finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with translucent plastic hoods until the plants had rooted. This cover causes uniform germination of the test plants, unless this was adversely affected by the active ingredients.

For the post-emergence treatment, the test plants were first grown to a height of 3 to 15 cm, depending on the plant habit, and only then treated with the active ingredients which were suspended or emulsified in water. For this purpose, the test plants were either sown directly and grown on in the same containers, or first grown separately as seedlings and transplanted into the experimental containers a few days before the treatment. The application rates for the post-emergence treatment was [sic] 125, 62.5, 7.81 and 3.91 g/ha of a.s. (active substance).

The plants were kept at temperatures from 10-25° C. or 20-35° C., depending on the species. The experimental period extended over 2 to 4 weeks. During this time, the plants were tended, and their response to the individual treatments was evaluated.

A scale from 0 to 100 was used for the evaluation. 100 means no emergence of the plants, or complete destruction of at least the aerial parts, while 0 means no damage, or normal growth.

The plants used in the greenhouse experiments were composed of the following species:

Scientific name Vernacular Name Abutilon theophrasti velvet leaf Amaranthus retroflexus redroot pigweed Chenopodium album lambsquarters (goosefoot) Commelina benghalensis bengal commelina; tropical spiderwort Ipomoca species morningglory Setaria faberii giant foxtail Solanum nigrum black nightshade Veronica species speedwell

At application rates of 7.81 and 3.91 g/ha active substance, the active ingredient No. 30 controlled Amaranthus retroflexus, Chenopodium album, Commelina benghalensis and Setaria faberii considerably better by the post-emergence method than the comparison compound A

At application rates of 125 and 62.5 g/ha active substance, the active ingredient No. 39 showed a considerably better herbicidal action against Abutilon theophrasti, Chenopodium album, Ipomoea species, Solanum nigrum and Veronica species in the post-emergence method than the comparison compound B 

We claim:
 1. A 1-aryl-4-thiotriazine of the formula I

where the variables have the following meanings: R¹ is methyl; R² is methyl; R³ is hydrogen or halogen; R⁴ is cyano or halogen; Y is the methine group; R⁵ is C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₃-C₆-cycloalkoxy, C₃-C₆-cycloalkylthio, C₂-C₆-alkenyloxy, C₂-C₆-alkenylthio, C₂-C₆-alkynyloxy or C₂-C₆-alkynylthio, optionally substituted by one of the following substituents: halogen, cyano, —CO—R⁸, —CO—OR⁸ or —CO—N(R⁸)—R⁹, —CO—R¹¹, —C(R¹¹)(OR¹³)(OR¹⁴), —C(R¹¹)═C(R¹⁵)—CO—R¹⁶, —CH(R¹¹)—CH(R¹⁵)—CO—R¹⁶, —CO—OR²⁰, —C(R¹⁰)═N—OR⁷, —N(R²¹)—R²² or —CO—N(R²¹)—R²²; R⁶ is hydrogen, halogen, C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, C₃-C₆-cycloalkyl or C₃-C₆-cycloalkoxy, optionally any of the last-mentioned 8 radicals, being substituted by one to three substituents, in each case selected from the group consisting of halogen, C₁-C₆-alkoxy and —CO—OR^(8′); R⁷ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, (C₁-C₆-alkoxy)carbonyl-C₁-C₆-alkyl or benzyl; R⁸, R^(8′) independently of one another are hydrogen, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, (C₁-C₆-alkoxy)carbonyl-C₁-C₆-alkyl, (C₃-C₆-alkenyloxy)carbonyl-C₁-C₆-alkyl, phenyl or phenyl-C₁-C₆-alkyl, it being possible for the phenyl group and the phenyl ring of the phenyl alkyl group to be unsubstituted or to have attached to them one to three radicals, in each case selected from the group consisting of halogen, nitro, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and (C₁-C₆-alkyl)carbonyl; R⁹ is hydrogen or C₁-C₆-alkyl; R¹⁰ is hydrogen, C₁-C₆-alkyl or C₁-C₆-alkoxy, it being possible for the 2 last-mentioned radicals to have attached to them one of the following substituents: C₁-C₆-alkoxy, (C₁-C₆-alkoxy)carbonyl or phenoxycarbonyl; R¹¹ is hydrogen, C₁-C₆-alkyl or C₁-C₆-haloalkyl; R¹³, R¹⁴ independently of one another are C₁-C₆-alkyl or together are a saturated 2- to 4-membered carbon chain which can have attached to it a C₁-C₆-alkyl radical; R¹⁵ is hydrogen, cyano, halogen or C₁-C₆-alkyl; R¹⁶ is O—R²³ or —N(R²¹)R²²; R²⁰, R²³ independently of one another are hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl or C₂-C₆-alkynyl, it being possible for any of the last-mentioned 4 groups to be substituted by one or two of the following radicals: cyano, halogen, hydroxyl, hydroxycarbonyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, (C₁-C₆-alkyl)carbonyl, (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkyl)carbonyloxy, (C₃-C₆-alkenyloxy)carbonyl, (C₃-C₆-alkynyloxy)carbonyl or phenyl or phenyl-C₁-C₆-alkyl, where the phenyl rings can be unsubstituted or, in turn, can have attached to them one to three substituents, in each case selected from the group consisting of cyano, nitro, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and (C₁-C₆-alkoxy)carbonyl; R²¹, R²² independently of one another are hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, (C₁-C₆-alkyl)carbonyl, (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkoxy)carbonyl-C₁-C₆-alkyl or C₁-C₆-alkylsulfonyl, or R²¹ and R²² together with the joint nitrogen atom, form a saturated or unsaturated 4- to 7-membered aza heterocycle which optionally contains one of the following members, in addition to carbon ring members: —O—, —S—, —N═, —NH— or —N(C₁-C₆-alkyl)—; or an agriculturally useful salt or enol ether of a compound I.
 2. A 1-aryl4-thiotriazine of the formula I as defined in claim 1 where Y together with R⁵ is a bridge >C—O—C(R⁶)═N—.
 3. A 1-aryl-4-thiotriazine of the formula I as defined in claim 1 where R⁵ is hydroxyl, 2) C₁-C₆-alkoxy, C₃-C₆-cycloalkoxy, C₂-C₆-alkenyloxy or C₂-C₆-alkynyloxy, it being possible for each of these 4 radicals optionally to have attached to it one of the following substituents: halogen, cyano, —CO—R⁸, —CO—OR⁸ or —CO—N(R⁸)R⁹.
 4. A 1-aryl-4-thiotriazine of the formula I as defined in claim 1 where R⁵ is mercapto, 2) C₁-C₆-alkylthio, C₃-C₆-cycloalkylthio, C₂-C₆-alkenylthio or C₂-C₆-alkynylthio, optionally any of the latter 4 radicals substituted by one of the following substituents: halogen, cyano, —CO—R⁸, —CO—OR⁸ or —CO—N(R⁸)R⁹.
 5. A 1-aryl-4-thiotriazine of the formula I as defined in claim 1 where R⁵ is C₁-C₆-alkyl, C₁-C₆-haloalkyl, 3) —CO—R¹¹, —C(R¹¹)(OR¹³)(OR¹⁴), —C(R¹¹)═C(R¹⁵)—CO—R¹⁶, —CH(R¹¹)—CH(R¹⁵)—CO—R¹⁶, —CO—OR²⁰, —C(R¹⁰)═N—OR⁷ or —CO—N(R²¹)—R²².
 6. A 1-aryl-4-thiotriazine of the formula 1 as defined in claim 1 where R⁵ is hydrogen, nitro, halogen or —N(R²¹)—R²².
 7. A herbicidal composition comprising a herbicidally active amount of at least one 1-aryl-4-thiotriazine of the formula I or of an agriculturally useful salt or enol ether of I as defined in claim 1 and at least one inert liquid and/or solid carrier and, if desired, at least one surfactant.
 8. A process for the preparation of herbicidally active compositions which comprises mixing a herbicidally active amount of at least one 1-aryl-4-thiotriazine of the formula I or of an agriculturally useful salt or enol ether of I as defined in claim 1 and at least one inert liquid and/or solid carrier and optionally at least one surfactant.
 9. A method of controlling undesired vegetion, which comprises allowing a herbicidally active amount of at least one 1-aryl-4-thiotriazine of the formula I or of an agriculturally useful salt or enol ether of I as defined in claim 1 to act on plants, their environment or on seed.
 10. A process for the preparation of a 1-aryl-4-thiotriazine of the formula I as defined in claim 1, wherein an isocyanate of the formula V

is reacted with a thiourea of the formula IV

 in the presence of an activated form of carbonic acid. 